Process for the preparation of pesticides

ABSTRACT

The invention relates to a process for the preparation of compounds of the formula ##STR1## or, if appropriate, a tautomer thereof, in each case in the free form or in salt form, in which 
     A, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 7 , R 9  and n are as defined in claim 1 and the C═N double bond marked with E has the E configuration, which comprises 
     a1) reacting either a compound of the formula (II) mentioned above with a compound of the formula (III) mentioned above, in which X 1  is a leaving group, or 
     a2) a compound of the formula (IV) mentioned above, if appropriate in the presence of a base, with a compound of the formula (V) mentioned above, or 
     b1) reacting a compound of the formula (VI) mentioned above with a compound of the formula R 7  --A--X 2  (VII), in which X 2  is a leaving group, and either further reacting the compound thus obtainable, of the formula (IV), for example according to method a2), or 
     b2) reacting it with hydroxylamine or a salt thereof, if appropriate in the presence of a basic or acid catalyst, and further reacting the compound thus obtainable, of the formula (II), for example according to method a1), or 
     c) reacting a compound of the formula (VII), mentioned above with a C 1  -C 6  alkyl nitrite and further reacting the compound thus obtainable, of the formula (VI), for example according to method b), the E isomers of the compounds of the formulae (II), (IV) and (VI), a process for their preparation and their use for the preparation of compounds of the formula (I).

The invention relates to a process for the preparation of compounds ofthe formula ##STR2## and, where appropriate, their tautomers, in eachcase in the free form or salt form, in which either

X is CH or N, Y is OR₁ and Z is O, or

X is N, Y is NHR₈ and Z is O, S or S(═O);

R₁ is C₁ -C₄ alkyl;

R₂ is H, C₁ -C₄ alkyl, halogeno-C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl or C₁-C₄ alkoxymethyl;

R₃ and R₄ independently of one another are H, C₁ -C₄ alkyl, C₁ -C₄alkoxy, OH, CN, NO₂, a (C₁ -C₄ alkyl)₃ --Si group, where the alkylgroups can be identical or different, halogen, (C₁ -C₄ alkyl)S(═O)_(m),(halogeno-C₁ -C₄ alkyl)S(═O)_(m), halogeno-C₁ -C₄ alkyl or halogeno-C₁-C₄ alkoxy;

R₅ is C₁ -C₆ alkyl, halogeno-C₁ -C₆ alkyl, C₁ -C₆ alkoxy, halogeno-C₁-C₆ alkoxy, C₁ -C₆ -alkylthio, halogen-C₁ -C₆ alkylthio, C₁ -C₆alkylsulfinyl, halogeno-C₁ -C₆ -alkylsulfinyl, C₁ -C₆ alkylsulfonyl,halogeno-C₁ -C₆ alkylsulfonyl, C₁ -C₆ alkoxy-C₁ -C₆ alkyl, halogeno-C₁-C₆ alkoxy C₁ -C₆ alkyl, C₁ -C₆ alkylthio-C₁ -C₆ alkyl, halogeno-C₁ -C₆alkylthio-C₁ -C₆ alkyl, C₁ -C₆ alkylsulfinyl-C₁ -C₆ alkyl, halogeno-C₁-C₆ -alkylsulfinyl-C₁ -C₆ alkyl, C₁ -C₆ -alkylsulfonyl-C₁ -C₆ alkyl,halogeno-C₁ -C₆ -alkylsulfonyl-C₁ -C₆ alkyl, C₁ -C₆ -alkylcarbonyl,halogeno-C₁ -C₆ -alkylcarbonyl, C₁ -C₆ -alkoxycarbonyl, halogeno-C₁ -C₆-alkoxycarbonyl, C₁ -C₆ -alkylaminocarbonyl, C₁ -C₄ -alkoxyiminomethyl;di(C₁ -C₆ alkyl)-aminocarbonyl, where the alkyl groups can be identicalor different; C₁ -C₆ -alkylaminothiocarbonyl; di(C₁ -C₆alkyl)-aminothiocarbonyl, where the alkyl groups can be identical ordifferent; C₁ -C₆ -alkylamino, di(C₁ -C₆ alkyl)-amino, where the alkylgroups can be identical or different; halogen, NO₂, CN, SF₅, thioamido,thiocyanatomethyl; an unsubstituted or mono- to tetrasubstituted C₁ -C₄alkylenedioxy group, where the substituents are selected from the groupconsisting of C₁ -C₄ alkyl and halogen; or QR₆, where, if n is greaterthan 1, the radicals R₅ can be identical or different;

R₆ is C₂ -C₆ alkenyl or C₂ -C₆ alkynyl which are unsubstituted orsubstituted by 1 to 3 halogen atoms; (C₁ -C₄ alkyl)₃ Si, where the alkylgroups can be identical or different; CN; or an unsubstituted or mono-to pentasubstituted C₃ -C₆ cycloalkyl, aryl or heterocyclyl group, wherethe substituents are selected from the group consisting of halogen, C₁-C₆ alkyl, halogeno-C₁ -C₆ alkyl, C₁ -C₆ alkoxy, halogeno-C₁ -C₆ alkoxy,phenoxy, naphthoxy and CN;

A either is a direct bond, C₁ -C₁₀ alkylene, --C(═O)--,--C(═S)-- orhalogeno-C₁ -C₁₀ alkylene and R₇ is a radical R₁₀, or is C₁ -C₁₀alkylene, --C(═O)--,--C(═S)-- or halogeno-C₁ -C₁₀ alkylene and R₇ isOR₁₀, N(R₁₀)₂, where the radicals R₁₀ can be identical or different, or--S(═O)_(q) R₁₀ ;

R₈ is H or C₁ -C₄ alkyl;

R₉ is methyl, fluoromethyl or difluoromethyl;

R₁₀ is H; an unsubstituted or substituted C₁ -C₆ alkyl, C₂ -C₆ alkenylor C₂ -C₆ alkynyl group, where the substituents are selected from thegroup consisting of halogen; (C₁ -C₄ alkyl)₃ Si, where the alkyl groupscan be identical or different; C₃ -C₆ cyclo-alkyl, which isunsubstituted or substituted by halogen; C₁ -C₆ alkoxycarbonyl, which isunsubstituted or substituted by halogen; unsubstituted or substitutedaryl, where the substituents are selected from the group consisting ofhalogen, halogeno-C₁ -C₄ alkyl and CN; a (C₁ -C₄ alkyl)₃ Si group, wherethe alkyl groups can be identical or different; C₃ -C₆ cycloalkyl, whichis unsubstituted or substituted by halogen; C₁ -C₆ alkoxycarbonyl whichis unsubstituted or substituted by halogen; or an unsubstituted orsubstituted aryl or heterocyclyl group, where the substituents areselected from the group consisting of halogen and halogeno-C₁ -C₄ alkyl;

Q is a direct bond, C₁ -C₈ alkylene, C₂ -C₆ alkenylene, C₂ -C₆alkynylene, O, O(C₁ -C₆ alkylene), (C₁ -C₆ alkylene)O, S(═O)_(p),S(═O)_(p) (C₁ -C₆ alkylene) or (C₁ -C₆ alkylene)S(═O)_(p) ;

m is 0, 1 or 2;

n is 0, 1, 2, 3, 4 or 5;

p is 0, 1 or 2; and

q is 0, 1 or 2,

and the C═N double bond marked with E has the E configuration,

which comprises

a1) reacting either a compound of the formula ##STR3## in which A, R₂,R₅, R₇ and n are as defined for formula I and the C═N double bond markedwith E has the E configuration, or a tautomer thereof, in each case inthe free form or in salt form, if appropriate in the presence of a base,with a compound of the formula ##STR4## which is known or can beprepared by methods known per se and in which X, Y, Z, R₃, R₄ and R₉ areas defined for formula I and X₁ is a leaving group, or a tautomerthereof, in each case in the free from or in salt form, or

a2) reacting a compound of the formula ##STR5## in which A, R₂, R₅, R₇and n are as defined for formula I and the C═N double bond marked with Ehas the E configuration, or a tautomer thereof, in each case in the freeform or in the salt form, if appropriate in the presence of a base, witha compound of the formula ##STR6## which is known or can be prepared bymethods known per se and in which X, Y, Z, R₃, R₄ and R₉ are as definedfor formula I, or a tautomer thereof, in each case in the free form orin salt form, or

b1) reacting a compound of the formula ##STR7## in which R₂, R₅ and nare as defined for formula I and the C═N double bond marked with E hasthe E configuration, or a tautomer thereof, in each case in the freeform or in salt form, if appropriate in the presence of a base, with acompound of the formula

    R.sub.7 --A--X.sub.2                                       (VII),

which is known or can be prepared by methods known per se and in which Aand R₇ are as defined for formula I and X₂ is a leaving group, andeither further reacting the compound thus obtainable, of the formula IV,for example according to method a2), or

b2) reacting it with hydroxylamine or a salt thereof, if appropriate inthe presence of a base or acid catalyst, and further reacting thecompound thus obtainable, of the formula II, for example according tomethod a1), or

c) reacting a compound of the formula ##STR8## which is known or can beprepared by methods known per se and in which R₂, R₅ and n are asdefined for formula I, or a tautomer thereof, in each case in the freeform or in salt form, if appropriate in the presence of a base, with aC₁ -C₆ alkyl nitrite, and further reacting the compound thus obtainable,of the formula VI, for example according to method b),

the E isomers of the compounds of the formulae II, IV and VI, or atautomer thereof, in each case in the free form or in salt form, aprocess for their preparation and their use for the preparation ofcompounds of the formula I.

The compounds of the formula I are known pesticides. The processes knownto date for their preparation give mixtures of E and Z isomers inrespect of the C═N double bond marked with E in formula I of differentcomposition, depending on the process. Since the biological propertiesof the E isomers are in each case found to be superior to those of themixtures and of the Z isomers, there is a need to develop preparationprocesses for compounds of the formula I having the isomerically pure Econfiguration. This object is achieved by the preparation processaccording to the invention.

Unless defined differently, the general terms used above and below aredefined as follows.

Carbon-containing groups and compounds in each case contain 1 up to andincluding 8, preferably 1 up to and including 6, in particular 1 up toand including 4, especially 1 or 2, carbon atoms.

Alkyl--as a group per se and as a structural element of other groups andcompounds, such as of halogenoalkyl, alkoxy, alkylthio, alkylsulfinyl,alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, halogenoalkoxycarbonyl,alkylaminocarbonyl, alkoxyiminomethyl, alkylaminothiocarbonyl andalkylamino--is, in each case taking into due consideration the number,included from case to case, of carbon atoms contained in thecorresponding group or compound, either straight-chain, i.e. methyl,ethyl, propyl, butyl, pentyl or hexyl, or branched, for exampleisopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl orisohexyl.

Alkenyl--as a group per se and as a structural element of other groupsand compounds, such as of halogenoalkenyl--is, in each case under dueconsideration of the number, included from case to case, of carbon atomscontained in the corresponding group or compound, either straight-chain,for example vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, orbranched, for example iso-propenyl.

Alkynyl--as a group per se and as a structural element of other groupsand compounds, such as of halogenoalkynyl--is, in each case under dueconsideration of the number, included from case to case, of carbon atomscontained in the corresponding group or compound, either straight-chain,for example propargyl, 2-butynyl or 5-hexynyl, or branched, for example2-ethynylpropyl or 2-propargylisopropyl.

C₃ -C₆ cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Alkylene--as a group per se and as a structural element of other groupsand compounds, such as of O(alkylene), (alkylene)O, S(═O)_(p)(alkylene), (alkylene)S(═O)_(p) or alkylenedioxy--is, in each case underdue consideration of the number, included from case to case, of carbonatoms contained in the corresponding group or compound, eitherstraight-chain, for example --CH₂ CH₂ --, --CH₂ CH₂ CH₂ -- or --CH₂ CH₂CH₂ CH₂ --, or branched, for example --CH(CH₃)--, --CH(C₂ H₅)--,--C(CH₃)₂ --, --CH(CH₃)CH₂ -- or --CH(CH₃)CH(CH₃)--.

Alkenylene is, in each case under due consideration of the number, fromcase to case, of carbon atoms contained in the corresponding compound,either straight-chain, for example vin-1,2-ylene, all-1,3-ylene,but-1-en-1,4-ylene or hex-2-en-1,6-ylene, or branched, for example1-methylvin-1,2-ylene.

Alkynylene is, in each case under due consideration of the number, fromcase to case, of carbon atoms contained in the corresponding compound,either straight-chain, for example propargylene, 2-butynylene or5-hexynylene, or branched, for example 2-ethynylpropylene or2-propargylisopropylene.

Aryl is phenyl or naphthyl, in particular phenyl.

Heterocyclyl is a 5- to 7-membered aromatic or non-aromatic ring havingone to three heteroatoms, which are selected from the group consistingof N, O and S. 5- and 6-membered rings which contain a nitrogen atom asa heteroatom and, if appropriate, a further heteroatom, preferablynitrogen or sulfur, in particular nitrogen, are preferred.

Halogen--as a group per se and as a structural element of other groupsand compounds, such as of halogenoalkyl, halogenoalkenyl andhalogenoalkynyl--is fluorine, chlorine, bromine or iodine, especiallyfluorine, chlorine or bromine, in particular fluorine or chlorine, veryespecially fluorine.

Halogen-substituted carbon-containing groups and compounds, such ashalogenoalkyl, halogenoalkenyl or halogenoalkynyl, can be partlyhalogenated or perhalogenated, and in the case of polyhalogenation, thehalogen substituents can be identical or different. Examples ofhalogenoalkyl--as a group per se and as a structural element of othergroups and compounds, such as of halogenoalkenyl--are methyl which ismono- to trisubstituted by fluorine, chlorine and/or bromine, such asCHF₂ or CF₃ ; ethyl which is mono- to pentasubstituted by fluorine,chlorine and/or bromine, such as CH₂ CF₃, CF₂ CF₃, CF₂ CCl₃, CF₂ CHCl₂,CF₂ CHF₂, CF₂ CFCl₂, CF₂ CHBr₂, CF₂ CHClF, CF₂ CHBrF or CClFCHClF;propyl or isopropyl which is mono- to heptasubstituted by fluorine,chlorine and/or bromine, such as CH₂ CHBrCH₂ Br, CF₂ CHFCF₃, CH₂ CF₂ CF₃or CH(CF₃)₂ ; and butyl or one of its isomers which is mono- tononasubstituted by fluorine, chlorine and/or bromine, such asCF(CF₃)--CHFCF₃ or CH₂ (CF₂)₂ CF₃. Halogenoalkenyl is, for example, CH₂CH═CHCl, CH₂ CH═CCl₂, CH₂ CF═CF₂ or CH₂ CH═CHCH₂ Br. Halogenoalkynyl is,for example, CH₂ C.tbd.CF, CH₂ C.tbd.CCH₂ Cl or CF₂ CF₂ C.tbd.CCH₂ F.

Some compounds I to VI and VIII can be present as tautomers, as isfamiliar to the expert, in particular if AR₇ is H. Compounds I above andbelow are therefore also to be understood as meaning correspondingtautomers, even if the latter are not mentioned specifically in eachcase.

Compounds I to VI and VIII which contain at least one basic centre, canform, for example, acid addition salts. These are formed, for example,with strong inorganic acids, such as mineral acids, for exampleperchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoricacid, or a hydrogen halide acid, with strong inorganic carboxylic acids,such as C₁ -C₄ alkanecarboxylic acids which are unsubstituted orsubstituted, for example by halogen, for example acetic acid, such asdicarboxylic acids which are saturated or unsaturated, for exampleoxalic, malonic, succinic, maleic, fumaric or phthalic acid, such ashydroxycarboxylic acids, for example ascorbic, lactic, malic, tartaricor citric acid, or such as benzoic acid, or with organic sulfonic acids,such as C₁ -C₄ alkane- or arylsulfonic acids which are unsubstituted orsubstituted, for example by halogen, for example methane- orp-toluenesulfonic acid. Compounds I with at least one acid group canfurthermore form salts with bases. Suitable salts with bases are, forexample, metal salts such as alkali metal or alkaline earth metal salts,for example sodium, potassium or magnesium salts, or salts with ammoniaor an organic amine, such as morpholine, piperidine, pyrrolidine, amono-, di- or tri-lower alkylamine, for example ethyl-, diethyl-,triethyl- or dimethyl-propyl-amine, or a mono-, di- or trihydroxy-loweralkylamine, for example mono-, di- or triethanolamine. Furthermore,where appropriate, corresponding inner salts can be formed.Agrochemically advantageous salts are preferred in the context of theinvention; however, salts which have disadvantages for agrochemicaluses, for example salts which are toxic to bees or fish, which areemployed, for example, for isolation or purification of free compounds Ior agrochemically usable salts thereof, are also included. Compounds ofthe formulae I to VI and VIII in the free form and in the form of theirsalts are also to be understood above and below as meaning thecorresponding salts or the free compounds I to VI and VIII. The sameapplies to tautomers of compounds of the formulae I to VI and VIII andsalts thereof. In general, the free form is in each case preferred.

The reactions described above and below are carried out in a mannerknown per se, for example in the absence or usually in the presence of asuitable solvent or diluent or a mixture thereof, the reaction beingcarried out, as required, with cooling, at room temperature or withheating, for example in a temperature range from about -80° C. up to theboiling point of the reaction medium, preferably from about 0° C. up toabout 150° C., and, if necessary, in a closed vessel, under pressure, inan inert gas atmosphere and/or under anhydrous conditions. Particularlyadvantageous reaction conditions can be seen from the examples.

The starting materials mentioned above and below, which are used for thepreparation of the compounds I, in each case in the free form or in saltform, are known or can be prepared by methods known per se, for examplein accordance with the following statements.

Variants a1/a2)

Suitable leaving groups X₁ in compounds III are, for example, hydroxyl,C₁ -C₈ alkoxy, halogeno-C₁ -C₈ alkoxy, C₁ -C₈ alkanoyloxy, mercapto, C₁-C₈ alkylthio, halogeno-C₁ -C₈ alkylthio, C₁ -C₈ alkanesulfonyloxy,halogeno-C₁ -C₈ alkanesulfonyloxy, benzenesulfonyloxy,toluenesulfonyloxy and halogen, preferably toluenesulfonyloxy,trifluoromethanesulfonyloxy and halogen, in particular halogen.

Suitable bases for facilitating the reaction are, for example, alkalimetal or alkaline earth metal hydroxides, hydrides, amides, alkanolates,acetates, carbonates, dialkylamides or alkylsilylamides, alkylamines,alkylenediamines, N-alkylated or non-alkylated, saturated or unsaturatedcycloalkylamines, basic heterocyclic compounds, ammonium hydroxides andcarbocyclic amines. Examples are sodium hydroxide, hydride, amide,methanolate, acetate and carbonate, potassium tert-butanolate,hydroxide, carbonate, and hydride, lithium diisopropylamide, potassiumbis(trimethylsilyl)amide, calcium hydride, triethylamine,diisopropyl-ethyl-amine, triethylenediamine, cyclohexylamine,N-cyclohexyl-N,N-dimethyl-amine, N,N-diethylaniline, pyridine,4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine,benzyl-trimethyl-ammonium hydroxide and1,5-diazabicyclo[5.4.0]undec-5-ene (DBU).

The reaction partners can be reacted with one another as such, i.e.without addition of a solvent or diluent, for example in the melt.However, the addition of an inert solvent or diluent or of a mixturethereof is usually advantageous. Examples of such solvents or diluentsare: aromatic, aliphatic and alicyclic hydrocarbons andhalogenohydrocarbons, such as benzene, toluene, xylene, mesitylene,tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether,hexane, cyclohexane, methylene chloride, chloroform, carbontetrachloride, dichloroethane, trichloroethene or tetrachloroethene;esters, such as ethyl acetate; ethers, such as diethyl ether, dipropylether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether,ethylene glycol monomethyl ether, ethylene glycol monoethyl ether,ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuranor dioxane; ketones, such as acetone, methyl ethyl ketone or methylisobutyl ketone; alcohols, such as methanol, ethanol, propanol,isopropanol, butanol, ethylene glycol or glycerol; amides, such asN,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide,N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles suchas acetonitrile or propionitrile; and sulfoxides, such as dimethylsulfoxide. If the reaction is carried out in the presence of a base,bases employed in excess, such as triethylamine, pyridine,N-methylmorpholine or N,N-diethylaniline, can also serve as the solventor diluent.

The reaction is advantageously carried out in a temperature range fromabout 0° C. up to about 180° C., preferably from about 10° C. up toabout 80° C., in many cases in the range between room temperature andthe reflux temperature of the reaction mixture.

The reaction is preferably carried out under normal pressure.

The reaction can be carried out without an inert gas atmosphere;preferably, however, it is carried out under an inert gas atmosphere,for example nitrogen or argon, in particular nitrogen.

The reaction time is not critical; a reaction time of about 0.1 to about24 hours, in particular about 0.5 to about 2 hours, is preferred.

The product is isolated by customary methods, for example by filtration,crystallization, distillation or chromatography or any suitablecombination of these processes.

In a preferred embodiment of variants a1/a2), a compound II is reactedwith a compound III at 0° C. to 80° C., preferably 10° C. to 30° C., inan inert solvent, preferably an amide, in particularN,N-dimethylformamide in the presence of a metal hydride, preferablysodium hydride.

Particularly preferred conditions for the reaction are described inExamples H 1d) and H 3f).

The compounds of the formula III are known or can be preparedanalogously to known compounds.

The compounds I are known. However, their preparation according to theprior art has a large number of serious industrial, ecological, economicand other disadvantages.

Thus, in the preparation processes according to the prior art, as a ruleE/Z isomer mixtures with respect to the C═N double bond marked with E informula I are obtained. Since the biological properties of the E isomersare in each case found to be superior to those of the mixtures and ofthe Z isomers in each case, the processes according to the prior arthave the significant disadvantage that products are produced which areeither significantly less active as E/Z mixtures or from which the Zisomers must be removed in order to increase their biological activity,which means that many unnecessary handling operations must be carriedout for separation of isomers, which has the effect of being verytime-consuming, blocks valuable production lines for a long time and isassociated with high additional energy costs. The removal of the lessactive Z isomer also leads to additional enormous losses in yield, whichin turn not only is problematic and ecologically disadvantageous, butalso renders the process according to the prior art much more expensiveand consequently economically of no interest. The industrial,ecological, economic and other disadvantages of the processes accordingto the prior art are not limited to those described above, these latterbeing intended to serve only as a few examples of the large number ofdisadvantages of the processes according to the prior art. Thedisadvantages of the processes according to the prior art cause seriousproblems even when the processes are carried out on a laboratory scale.When the processes are carried out on a larger scale, thesedisadvantages intensify considerably. In the end, however, the aim is tocarry out a specific process on an industrial scale if this process isto be suitable for preparing products for agrochemical purposes.

According to the process of the present invention, the compounds I areprepared by reaction of the compound II with a compound III or byreaction of the compound IV with a compound V. These processes accordingto the invention have extremely surprising industrial, ecological,economic and other advantages compared with the processes from the priorart. Since the compounds II or, respectively, IV are present in thepreparation process according to the invention as pure E isomers inrespect of the C═N double bond marked with E, only the E isomer of thecompounds I is produced in the present process, which has the effect ofan enormous saving in time and at the same time a high saving in costand energy, since no valuable production lines are blocked for a longtime for separation of the isomers, and at the same time the amount ofbiologically more active E isomer produced by per unit time is muchhigher than in the processes according to the prior art. The resourcessuch as starting products and energy are consequently utilized to theoptimum in the present process, which not only very greatly simplifiesthe process and renders it ecologically advantageous, but consequentlyrenders it cheaper and therefore of greater economic interest. Thismeans that all the disadvantages of the processes according to the priorart which can be attributed to the formation of E/Z isomers are avoided.The industrial, ecological, economic and other advantages of the processaccording to the invention are not limited only to those describedabove, these latter being intended to serve only as a few examples ofthe large number of advantages inherent in this process. Due to all theabovementioned advantages of the present process, the serious problemswhich occur in the processes according to the prior art are avoided evenat the stage of a laboratory process. If the present process is used ona larger scale, these advantages prove to be even much more significant,which has the effect that these advantages first allow the process to beused on an industrial scale.

For this reason, all the industrial, ecological, economic and otherdisadvantages of the processes according to the prior art aresurprisingly advantageously overcome in the preparation of compounds Iby the present process.

Variant b)

The process according to variant b) is carried out by first reactingcompound VI with compound VII, if appropriate further reacting theresulting product IV, if appropriate after isolation, with hydroxylamineor a salt thereof, and further reacting the resulting products II or,respectively, IV, if appropriate after isolation, in accordance withvariants a1/a2), for example in the manner described above, to give thecompounds I.

Suitable leaving groups X₂ in the compounds VII are, for example, thosewhich are mentioned as examples for X₁ in variants a1/a2).

Suitable bases for facilitating the reaction are, for example, thosewhich are mentioned in variants a1/a2).

The reaction partners can be reacted with one another as such, i.e.without addition of a solvent or diluent, for example in the melt.However, the addition of an inert solvent or diluent or of a mixturethereof is usually advantageous. Examples of such solvents or diluentsare those mentioned in variants a1/a2).

The reaction is advantageously carried out in a temperature range fromabout 0° C. to about 180° C., preferably from about 10° C. to about 80°C., in many cases in the range between room temperature and the refluxtemperature of the reaction mixture.

The reaction is preferably carried out under normal pressure.

The reaction can be carried out without an inert gas atmosphere;preferably, however, it is carried out under an inert gas atmosphere,for example nitrogen or argon, in particular nitrogen.

The reaction time is not critical; a reaction time of about 0.1 to about24 hours, in particular about 0.5 to about 5 hours, is preferred.

The product is isolated by customary methods, for example filtration,crystallization, distillation or chromatography or any suitablecombination of these processes.

In a preferred embodiment of variant b), a compound VI is reacted with acompound VII at 0° C. to 80° C., preferably 10° C. to 60° C., in aninert solvent, preferably a nitrile, in particular acetonitrile, in thepresence of a metal carbonate, preferably potassium carbonate, and thecompound IV thus obtainable is then further reacted, preferably inaccordance with method a2).

Particularly preferred conditions for the reaction are described inExamples H 1b) to 1d) and H 3d) to 3f).

The compounds of the formula VII are known or can be preparedanalogously to known compounds.

The present process according to the invention of variant b), which inprinciple is an advantageous combination of an O-alkylation reactionwith process variants a1/a2) according to the invention, has all thegreat advantages compared with the prior art which have already beendiscussed above for the process according to the invention of variantsa1/a2). In particular, the process of variant b) ensures that the Econfiguration of the C═N double bond marked with E in compound VI isretained. Furthermore, however, the process according to the inventionof variant b) also has further industrial, ecological, economic andother advantages which are connected with the specific property that theintermediate product IV initially formed is not purified but is directlyfurther processed as the moist crude product, in the case ofintermediate isolation, or in situ in the reaction mixture, if it is notisolated. This missing purification step on the intermediate productmentioned is of advantage, for example, in as much as it is notnecessary to dry it, which not only saves energy and further resources,but also enormously increases the safety of the preparation process,since the possible danger of a dust explosion of the dry intermediateproduct is averted completely. The savings in resources are even greaterif the intermediate product is further reacted without purification,since, for example, no additional solvents are consumed for therecrystallization. The process of variant b) is of particular advantagecompared with the individual process steps of the alkylation reaction ofvariants a1/a2) carried out in that the total reaction time in theprocess of variant b) is much shorter, which consequently leads to amuch higher production of reaction product I per unit time and thereforeto a much more efficient utilization of the valuable production lines.Furthermore, the total yield of reaction product I is surprisingly goodwhen the process of variant b) is employed, and, compared with thecombined yields of the individual process steps of the alkylationreaction and variants a1/a2) carried out, is in the same percentagerange or even beffer. The industrial, ecological, economic and otheradvantages of the process according to the invention of variant b) arenot limited to those described above, these latter being intended toserve only as a few examples of the large number of advantages inherentin the process according to the invention of variant b).

By using process variant b) according to the invention for preparationof the compounds I, a large number of industrial, ecological, economicand other advantages can therefore surprisingly be utilized efficiently.

Variant c)

The process according to variant c) is carried out by first reactingcompound VIII with an alkylnitrite and further reacting the resultingproduct VI, if appropriate after isolation, in accordance with variantb), for example in the manner described above, to give the compounds I.

Suitable bases for facilitating the reaction are, for example, thosewhich are mentioned in variants a1/a2).

The reaction partners can be reacted with one another as such, i.e.without addition of a solvent or diluent, for example in the melt.However, the addition of an inert solvent or diluent or of a mixturethereof is usually advantageous. Examples of such solvents or diluentsare those mentioned in variants a1/a2).

The reaction is advantageously carried out in a temperature range fromabout 0° C. to about 180° C., preferably from about 0° C. to about 60°C., in many cases in the range between room temperature and the refluxtemperature of the reaction mixture.

The reaction is preferably carried out under normal pressure.

The reaction can be carried out without an inert gas atmosphere;preferably, however, it is carried out under an inert gas atmosphere,for example nitrogen or argon, in particular nitrogen.

The reaction time is not critical; a reaction time of about 0.1 to about24 hours, in particular about 0.5 to about 3 hours, is preferred.

The product is isolated by customary methods, for example filtration,crystallization, distillation or chromatography or any suitablecombination of these processes.

In a preferred embodiment of variant c), a compound VIII is reacted withan alkyl nitrite at 0° C. to 80° C., preferably 0° C. to 40° C., in aninert solvent, preferably an alcohol, in particular methanol, in thepresence of a metal alcoholate, preferably sodium methanolate, and thecompound VI thus obtainable is then further reacted, preferably inaccordance with method b).

Particularly preferred conditions for the reactions are described inExamples H 3d) to 3f).

The compounds of the formula VIII are known or can be preparedanalogously to known compounds.

The present process according to the invention of variant c), which inprinciple is an advantageous combination of an oximation reaction withprocess variants a1/a2) and b) according to the invention, has all thegreat advantages compared with the prior art which have already beendiscussed above for the processes according to the invention of variantsa1/a2) and b). Furthermore, the present oximation process for thepreparation of the compounds VI surprisingly result exclusively in the Econfiguration of the C═N double bond marked with E in formula VI. It isthus ensured that the particular starting products II, IV or,respectively, VI in the subsequent processes according to the inventionfor the preparation of the compounds I, for example in process variantsa1/a2) and b), are pure E isomers.

A large number of industrial, ecological, economic and other advantagescan therefore surprisingly be utilized efficiently by using processvariants c) according to the Invention for the preparation of thecompounds of the formula I.

The E isomers of the compounds of the formulae II, IV and VI andtautomers thereof, in each case in the free form or in salt form, arenovel and the present invention likewise relates to them.

The present invention furthermore relates to a process for thepreparation of the E isomers of a compound of the formula VI or of atautomer thereof, in each case in the free form or in salt form,according to the abovementioned process c),

a process for the preparation of the E isomers of a compound of theformula IV, or of a tautomer thereof, in each case in the free form orin salt form, according to the abovementioned process b1), and

a process for the preparation of the E isomers of a compound of theformula II, or of a tautomer thereof, in each case in the free form orin salt form, according to the abovementioned process b2).

The process conditions for the preparation of these intermediateproducts can be seen from the abovementioned processes a), b) and c).

PREPARATION EXAMPLE Example H1 Methyl2-[[[(1-methyl-2-phenyl-2-E-[(2-propynyl)oxyimino]-ethylidene)amino]oxy]methyl]α-(methoxymethylene)-phenylacetate(Compound 1.16)

H1a) 1-Phenyl-1,2-propanedione 1-E-oxime

69.7 g of a 30% solution of sodium methylate in methanol are addeddropwise to a solution of 40.2 g of 1-phenyl-2-propanone and 36.1 g ofisopentyl nitrite in 460 ml of methanol at 20-25°, while cooling. Thereaction mixture is then further stirred at room temperature for 1 hour.After the solution has been concentrated in vacuo, the residue isdissolved in 600 ml of water, the solution is acidified with 10%hydrochloric acid, the product which precipitates out is filtered offand dissolved in ethyl acetate and the organic phase is washed twicewith water, dried with sodium sulfate and evaporated in vacuo. Theresidue is stirred up in hexane and filtered. The title product is thusobtained with a melting of 168-70° C.

H1b) 1-Phenyl-1,2-propanedione 1-E-[(2-propynyl)oxime]

A mixture of 14 g of 1-phenyl-1,2-propanedione 1-E-oxime, 11.9 g of1-bromo-2-propyne, 13.8 g of potassium carbonate and 0.5 g of potassiumiodide in 170 ml of acetonitrile is stirred at 50° for 2 hours, thesolvent is then distilled off in vacuo and the residue is dissolvedagain in ethyl acetate. The organic phase is washed in each case twicewith water and saturated sodium chloride solution, dried with sodiumsulfate and evaporated in vacuo. After recrystallization of the residuefrom hexane, 1-phenyl-1,2-propanedione 1-E-[(2-propynyl)oxime] isobtained with a melting point of 54-56° C.

H1d) 1-Phenyl-1,2-propanedione 1-E-[(2-propynyl)oxime]-2-oxime

A mixture of 14.3 g of 1-phenyl-1,2-propanedione1-E-[(2-propynyl)oxime], 10.3 g of hydroxylamine hydrochloride and 11.7g of pyridine in 230 ml of ethanol is boiled under reflux for 1 hour andthen concentrated in vacuo, and 800 ml of water are added to theresidue. The product which has precipitated out is filtered off anddissolved in ethyl acetate and the solution is washed three times withwater, dried with sodium sulfate and evaporated in vacuo. The residue issuspended in hexane and filtered. The title product is thus obtainedwith a melting point of 163-165° C.

H1e) Methyl2-[[[(1-methyl-2-phenyl-2-E-[(2-propynyl)oxyimino]ethy-lidene)amino]oxy]-methyl]-α-(methoxymethylene)-phenylacetate

A solution of 5 g of 1-phenyl-1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime in 24 ml of N,N-dimethylformamide isadded dropwise to a suspension of 1.16 g of sodium hydride (about 55% inoil) in 45 ml of N,N-dimethylformamide at room temperature and themixture is further stirred for 10 minutes. 6.5 g of methyl2-(bromomethyl)-α-(methoxymethylene)-phenylacetate in 24 ml ofN,N-dimethylformamide are then added dropwise and the reaction mixtureis further stirred at room temperature for 1 hour. Thereafter, themixure is acidified with acetic acid and evaporated in vacuo. Theresidue is dissolved in ethyl acetate and the solution is washed threetimes with water and twice with saturated sodium chloride solution,dried with sodium sulfate and evaporated in vacuo. Afterrecrystallization of the residue from hexane/ethyl acetate, the titlecompound is obtained with a melting point of 82-84°.

Example H2 Methyl2-[[[(1-methyl-2-(4-fluorophenyl)-2-E-[(2-propynyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate(compound 1.44)

The title compound with a melting point of 91-93° can be prepared in amanner analogous to that described in Example H1, starting from1-(4-fluorophenyl)-2-propanone.

Example H3 Methyl2-[[[(1-methyl-2-(4-(3-trifluoromethylphenylmethoxy)-phenyl)2-E-[(2propynyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate(compound 1.240)

H3a) 1-(4-Hydroxyphenyl)-2-propanone

A mixture of 82 g of 1-(4-methoxyphenyl)-2-propanone, 500 ml of aceticacid and 500 ml of aqueous hydrobromic acid is boiled under reflux for 2hours and then evaporated in vacuo. The oily residue is extracted fourtimes with 700 ml of hexane/ether (5:2) each time, the extract isevaporated and the residue is chromatographed over silica gel usinghexane/ethyl acetate (3:1). 1-(4-Hydroxyphenyl)-2-propanone is thusobtained with a melting point of 40-41°.

H3b) 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]-2-propanone

A mixture of 5.8 g of 1-(4-hydroxyphenyl)-2-propanone, 61.6 g ofpotassium carbonate, 72.3 g of1-(chloromethyl)-3-(trifluoromethyl)-benzene, and 1 g of potassiumiodide in 800 ml of acetone is boiled under reflux for 5 hours.Thereafter, the reaction mixture is filtered and the filtrate isevaporated in vacuo. The residue is then dissolved in diethyl ether andthe ethereal phase is washed three times with water, dried with sodiumsulfate and evaporated. The1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-2-propanone thusobtainable is employed in the next reaction stage without furtherpurification.

H3c) 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-oxime

45 g of a 30% solution of sodium methanolate in methanol are slowlyadded dropwise to a solution of 59.6 g of1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-2-propanone and 23.4 g ofisopentyl nitrite in 300 ml of methanol such that the temperature doesnot exceed 20-25°. The reaction mixture is then further stirred at roomtemperature for 1 hour and thereafter evaporated in vacuo. The residueis dissolved in 600 ml of water and the solution is acidified with 10%hydrochloric acid. The precipitate which separates out is filtered offand dissolved in ethyl acetate and the organic phase is washed twicewith water, dried with sodium sulfate and evaporated. After the crudeproduct has been suspended in hexane and filtered,1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione 1-E-oximeis obtained with a melting point of 134-136°.

H3d) 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime]

A mixture of 6 g of1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-oxime, 2.4 g of 1-bromo-2-propyne, 2.6 g of potassium carbonate and0.5 g of potassium iodide in 40 ml of acetonitrile is boiled underreflux for 1 hour and then evaporated in vacuo and the residue isdissolved in ethyl acetate. The organic phase is washed twice with waterand once with saturated sodium chloride solution, dried with sodiumsulfate and evaporated. The crude1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime] thus obtainable is further processed withoutfurther purification.

H3e) 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime

A mixture of 5.9 g of1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime], 2.3 g of hydroxylamine hydrochloride and 2.6 gof pyridine in 60 ml of ethanol is boiled under reflux for 1 hour andthen concentrated in vacuo, and 200 ml of water are added to theresidue. The product which has precipitated out is filtered off anddissolved in ethyl acetate, and the solution is washed twice with waterand once with saturated sodium chloride solution, dried with sodiumsulfate and evaporated in vacuo. The residue is suspended in hexane andfiltered. 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime is thus obtained with a melting point of114-115°.

H3f) Methyl2-[[[(1-methyl-2-(4-(3-trifluoromethylphenylmethoxy)-phenyl)-2-E-[(2-propynyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate

A solution of 5.5 g of1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime in 25 ml of N,N-dimethylformamide isadded dropwise to a suspension of 0.7 g of sodium hydride (about 55% inoil) in 25 ml of N,N-dimethylformamide and the mixture is furtherstirred at room temperature for 10 minutes. 4 g of methyl2-(bromomethyl)-α-(methoxymethylene)-phenylacetate in 15 ml ofN,N-dimethylformamide are then added dropwise and the reaction mixtureis further stirred at room temperature for 1 hour. Thereafter, themixture is acidified with acetic acid and evaporated in vacuo at 50°.The residue is dissolved in ethyl acetate and the solution is washedtwice with water and once with saturated sodium chloride solution, driedwith sodium sulfate and evaporated in vacuo. After purification bychromatography (silica gel, ethyl acetate/hexane 1:3), the titlecompound is obtained as a resin.

Example H4 Methyl2-[[[(1-methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate(compound 1.366)

H4a) 1-[4-(4-Chlorophenoxy)-phenyl]-1,2-propanedione 1-E-oxime

16.7 g of a 30% solution of sodium methylate in methanol are addeddropwise to a solution of 22.5 g of1-[4-(4-chlorophenoxy)-phenyl]-2-propanone and 10.3 g of isopentylnitrite in 120 ml of methanol at 20-25°, while cooling. The reactionmixture is then further stirred at room temperature for 1 hour. Afterthe solution has been concentrated in vacuo, the residue is dissolved in300 ml of water and the solution is acidified with 10% hydrochloricacid, the product which precipitates out is filtered off and dissolvedin ethyl acetate and the organic phase is washed twice with water, driedwith sodium sulfate and evaporated in vacuo. The residue is stirred upin hexane and filtered. The title product is thus obtained with amelting point of 154-155° C.

H4b) 1-[4-(4-Chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-ethyl)oxime]

A mixture of 6 g of) 1-[4-(4-Chlorophenoxy)-phenyl]-1,2-propanedione1-E-oxime, 3.3 g of ethyl bromide, 3.5 g of potassium carbonate and 0.5g of potassium iodide in 30 ml of acetonitrile is stirred at 50° for 2hours, the solvent is then distilled off in vacuo and the residue isdissolved again in ethyl acetate. The organic phase is washed in eachcase twice with water and saturated sodium chloride solution, dried withsodium sulfate and evaporated in vacuo. After recrystallization of theresidue from hexane, the title product is obtained with a melting pointof 77-78° C.

H4c) 1-[4-(4-Chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-ethyl)oxime]-2-oxime

A mixture of 5.5 g of 1-[4-(4-chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-ethyl)oxime], 2.4 g of hydroxylamine hydrochloride and 2.7 9 ofpyridine in 50 ml of ethanol is boiled under reflux for 1 hour and thenconcentrated in vacuo, and 800 ml of water are added to the residue. Theproduct which has precipitated out is filtered off and dissolved inethyl acetate and the solution is washed three times with water, driedwith sodium sulfate and evaporated in vacuo. The residue is suspended inhexane and filtered. The title product is thus obtained in a pure formwith a melting point of 176-177° C.

H4d) Methyl2-[[[(1-methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate.

A solution of 4.7 g of 1-[4-(4-chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)-oxime]-2-oxime in 25 ml of N,N-dimethylformamide isadded dropwise to a suspension of 0.65 g of sodium hydride (about 55% inoil) in 20 ml of N,N-dimethylformamide and the mixture is furtherstirred at room temperature for 10 minutes. 4 g of methyl2-(bromomethyl)-α-(methoxymethylene)-phenylacetate in 15 ml ofN,N-dimethylformamide are then added dropwise and the reaction mixtureis further stirred at room temperature for 1 hour. Thereafter, themixture is acidified with acetic acid and evaporated in vacuo at 50°.The residue is dissolved in ethyl acetate and the solution is washedtwice with water and once with saturated sodium chloride solution, driedwith sodium sulfate and evaporated in vacuo. After purification by flashchromatography (silica gel, ethyl acetate/hexane 1:3), the titlecompound is obtained with a melting point of 87-89° C.

Example H5 Methyl2-[[[(1-methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxyimino)-phenylacetate(compound 2.366)

The title compound with a melting point of 90 to 93° C. is obtained in amanner analogous to that described in Example H4 from1-[4-(4-chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime and methyl2-(bromomethyl)-α-(methoxyimino)-phenylacetate.

Example H62-[[[(1-Methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxyimino)-phenylaceticacid methylamide (compound 3.366)

13,3 g of methyl2-[[[(1-methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxyimino]ethyliene)amino]oxy]methyl]-α-(methoxyimino)-phenylacetateare left to stand together with 80 ml of dimethylformamide and 9.2 ml ofan 8 molar solution of methylamine in ethanol at room temperature fortwo days. The mixture is concentrated at 50° C., n-hexane is added andthe mixture is cooled to room temperature and filtered. The residue isdried under a high vacuum. The title compound is obtained with a meltingpoint of 126-129° C.

Example H7

The other compounds listed in Tables 1 to 3 can also be prepared in amanner analogous to that described in Examples H1 to H6. In the"physical data" column of the tables, the temperatures stated in eachcase designate the melting point of the compound in question. c.propylis cyclopropyl.

                  TABLE 1                                                         ______________________________________                                             Compounds of the general formula                                         ______________________________________                                                                       I.1                                                                            ##STR9##                                      ______________________________________                                    

in which X is CH and Y is oxygen and the combination of substituents R₂,(R₅)_(n) and A--R₇ for a compound in each case corresponds to a line inTable A. The compound numbers of the following table correspond to theparticular numbers in Table A.

    ______________________________________                                        Compound No.    Phys. Data( Melting point ° C.)                        ______________________________________                                        1.14            75-77°                                                   1.16 82-84°                                                            1.22 111-113°                                                          1.42 Resin                                                                    1.44 91-93°                                                            1.50 Resin                                                                    1.70 Resin                                                                    1.72 Resin                                                                    1.78 Resin                                                                    1.225 102-113°                                                         1.226 81-83°                                                           1.227 Resin                                                                   1.233 Resin                                                                   1.234 73-75°                                                           1.238 Resin                                                                   1.240 Resin                                                                   1.241 Resin                                                                   1.242 Resin                                                                   1.244 Resin                                                                   1.245 Resin                                                                   1.294 Resin                                                                   1.296 112-114°                                                         1.366 87-89°                                                         ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                        Compounds of the general formula I.1, in which                                  X is nitrogen and                                                             Y is oxygen                                                                   and the combination of substituents R.sub.2, (R.sub.5).sub.n  and           A-R.sub.7  for                                                                  a compound in each case corresponds to a line in Table A.                          Compound No.                                                                             Melting point (° C.)                                 ______________________________________                                        2.198         75-77                                                             2.254 80-82                                                                   2.309 106-108                                                                 2.310 102-104                                                                 2.366 90-93                                                                 ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                        Compounds of the general formula I.1, in which                                  X is nitrogen and                                                             Y is NH and                                                                   the combination of substituents R.sub.2, (R.sub.5).sub.n  and A-R.sub.7      for                                                                           a compound in each case corresponds to a line in Table A.                           Compound No.                                                                             Melting point (° C.)                                 ______________________________________                                        3.198         75-77                                                             3.254 112-114                                                                 3.309 89-91                                                                   3.310 88-90                                                                   3.366 126-129                                                               ______________________________________                                    

                  TABLE A                                                         ______________________________________                                        Compound                                                                        No. R.sub.2 (R.sub.5).sub.n A-R.sub.7                                       ______________________________________                                         1       CH.sub.3                                                                             H              CH.sub.3                                          2 CH.sub.3 H C.sub.2 H.sub.5                                                  3 CH.sub.3 H n-C.sub.3 H.sub.7                                                4 CH.sub.3 H i-C.sub.3 H.sub.7                                                5 CH.sub.3 H n-C.sub.4 H.sub.9                                                6 CH.sub.3 H n-C.sub.6 H.sub.13                                               7 CH.sub.3 H CH.sub.2 F                                                       8 CH.sub.3 H CHF.sub.2                                                        9 CH.sub.3 H CH.sub.2 CF.sub.3                                                10 CH.sub.3 H CH.sub.2 CH=CH.sub.2                                            11 CH.sub.3 H CH.sub.2 CH=CHCH.sub.3                                          12 CH.sub.3 H CH.sub.2 CH=C(CH.sub.3).sub.2                                   13 CH.sub.3 H CH.sub.2 CH=CHCl                                                14 CH.sub.3 H CH.sub.2 CH=CCl.sub.2                                           15 CH.sub.3 H CH.sub.2 C(CH.sub.3)=CH.sub.2                                   16 CH.sub.3 H CH.sub.2 C=CH                                                   17 CH.sub.3 H CH.sub.2 Si(CH.sub.3).sub.3                                     18 CH.sub.3 H CH.sub.2 -c.propyl-2,2-Cl.sub.2                                 19 CH.sub.3 H CH.sub.2 CN                                                     20 CH.sub.3 H CH.sub.2 COOC.sub.2 H.sub.5                                     21 CH.sub.3 H CH(CH.sub.3)COOC.sub.2 H.sub.5                                  22 CH.sub.3 H CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3                            23 CH.sub.3 H CH.sub.2 C.sub.6 H.sub.4 -4-F                                   24 CH.sub.3 H CH.sub.2 C.sub.6 H.sub.4 -3-F                                   25 CH.sub.3 H CH.sub.2 C.sub.6 H.sub.4 -2-F                                   26 CH.sub.3 H C(=O)OC.sub.2 H.sub.5                                           27 CH.sub.3 H C(=O)NHCH.sub.3                                                 28 CH.sub.3 H C(=O)C(=O)OC.sub.2 H.sub.5                                      29 CH.sub.3 4-F CH.sub.3                                                      30 CH.sub.3 4-F C.sub.2 H.sub.5                                               31 CH.sub.3 4-F n-C.sub.3 H.sub.7                                             32 CH.sub.3 4-F i-C.sub.3 H.sub.7                                             33 CH.sub.3 4-F n-C.sub.4 H.sub.9                                             34 CH.sub.3 4-F n-C.sub.6 H.sub.13                                            35 CH.sub.3 4-F CH.sub.2 F                                                    36 CH.sub.3 4-F CHF.sub.2                                                     37 CH.sub.3 4-F CH.sub.2 CF.sub.3                                             38 CH.sub.3 4-F CH.sub.2 CH=CH.sub.2                                          39 CH.sub.3 4-F CH.sub.2 CH=CHCH.sub.3                                        40 CH.sub.3 4-F CH.sub.2 CH=C(CH.sub.3).sub.2                                 41 CH.sub.3 4-F CH.sub.2 CH=CHCl                                              42 CH.sub.3 4-F CH.sub.2 CH=CCl.sub.2                                         43 CH.sub.3 4-F CH.sub.2 C(CH.sub.3)=CH.sub.2                                 44 CH.sub.3 4-F CH.sub.2 C=CH                                                 45 CH.sub.3 4-F CH.sub.2 Si(CH.sub.3).sub.3                                   46 CH.sub.3 4-F CH.sub.2 -c.propyl-2,2-Cl.sub.2                               47 CH.sub.3 4-F CH.sub.2 CN                                                   48 CH.sub.3 4-F CH.sub.2 COOC.sub.2 H.sub.5                                   49 CH.sub.3 4-F CH(CH.sub.3)COOC.sub.2 H.sub.5                                50 CH.sub.3 4-F CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3                          51 CH.sub.3 4-F CH.sub.2 C.sub.6 H.sub.4 -4-F                                 52 CH.sub.3 4-F CH.sub.2 C.sub.6 H.sub.4 -3-F                                 53 CH.sub.3 4-F CH.sub.2 C.sub.6 H.sub.4 -2-F                                 54 CH.sub.3 4-F C(=O)OC.sub.2 H.sub.5                                         55 CH.sub.3 4-F C(=O)NHCH.sub.3                                               56 CH.sub.3 4-F C(=O)C(=O)OC.sub.2 H.sub.5                                    57 CH.sub.3 4-OCH.sub.3 CH.sub.3                                              58 CH.sub.3 4-OCH.sub.3 C.sub.2 H.sub.5                                       59 CH.sub.3 4-OCH.sub.3 n-C.sub.3 H.sub.7                                     60 CH.sub.3 4-OCH.sub.3 i-C.sub.3 H.sub.7                                     61 CH.sub.3 4-OCH.sub.3 n-C.sub.4 H.sub.9                                     62 CH.sub.3 4-OCH.sub.3 n-C.sub.6 H.sub.13                                    63 CH.sub.3 4-OCH.sub.3 CH.sub.2 F                                            64 CH.sub.3 4-OCH.sub.3 CHF.sub.2                                             65 CH.sub.3 4-OCH.sub.3 CH.sub.2 CF.sub.3                                     66 CH.sub.3 4-OCH.sub.3 CH.sub.2 CH=CH.sub.2                                  67 CH.sub.3 4-OCH.sub.3 CH.sub.2 CH=CHCH.sub.3                                68 CH.sub.3 4-OCH.sub.3 CH.sub.2 CH=C(CH.sub.3).sub.2                         69 CH.sub.3 4-OCH.sub.3 CH.sub.2 CH=CHCl                                      70 CH.sub.3 4-OCH.sub.3 CH.sub.2 CH=CCl.sub.2                                 71 CH.sub.3 4-OCH.sub.3 CH.sub.2 C(CH.sub.3)=CH.sub.2                         72 CH.sub.3 4-OCH.sub.3 CH.sub.2 C=CH                                         73 CH.sub.3 4-OCH.sub.3 CH.sub.2 Si(CH.sub.3).sub.3                           74 CH.sub.3 4-OCH.sub.3 CH.sub.2 -c. propyl-2,2-Cl.sub.2                      75 CH.sub.3 4-OCH.sub.3 CH.sub.2 CN                                           76 CH.sub.3 4-OCH.sub.3 CH.sub.2 COOC.sub.2 H.sub.5                           77 CH.sub.3 4-OCH.sub.3 CH(CH.sub.3)COOC.sub.2 H.sub.5                        78 CH.sub.3 4-OCH.sub.3 CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3                  79 CH.sub.3 4-OCH.sub.3 CH.sub.2 C.sub.6 H.sub.4 -4-F                         80 CH.sub.3 4-OCH.sub.3 CH.sub.2 C.sub.6 H.sub.4 -3-F                         81 CH.sub.3 4-OCH.sub.3 CH.sub.2 C.sub.6 H.sub.4 -2-F                         82 CH.sub.3 4-OCH.sub.3 C(=O)OC.sub.2 H.sub.5                                 83 CH.sub.3 4-OCH.sub.3 C(=O)NHCH.sub.3                                       84 CH.sub.3 4-OCH.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5                            85 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.3                                       86 CH.sub.3 4-OC.sub.2 H.sub.5 C.sub.2 H.sub.5                                87 CH.sub.3 4-OC.sub.2 H.sub.5 n-C.sub.3 H.sub.7                              88 CH.sub.3 4-OC.sub.2 H.sub.5 i-C.sub.3 H.sub.7                              89 CH.sub.3 4-OC.sub.2 H.sub.5 n-C.sub.4 H.sub.9                              90 CH.sub.3 4-OC.sub.2 H.sub.5 n-C.sub.6 H.sub.13                             91 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 F                                     92 CH.sub.3 4-OC.sub.2 H.sub.5 CHF.sub.2                                      93 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 CF.sub.3                              94 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 CH=CH.sub.2                           95 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 CH=CHCH.sub.3                         96 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 CH=C(CH.sub.3).sub.2                  97 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 CH=CHCl                               98 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 CH=CCl.sub.2                          99 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 C(CH.sub.3)=CH.sub.2                 100 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 C=CH                                 101 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 Si(CH.sub.3).sub.3                   102 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 -c.propyl-2,2-Cl.sub.2                                             103 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2                                     CN                                               104 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 COOC.sub.2 H.sub.5                   105 CH.sub.3 4-OC.sub.2 H.sub.5 CH(CH.sub.3)COOC.sub.2 H.sub.5                106 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3                                        107 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2                                     C.sub.6 H.sub.4 -4-F                             108 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 C.sub.6 H.sub.4 -3-F                 109 CH.sub.3 4-OC.sub.2 H.sub.5 CH.sub.2 C.sub.6 H.sub.4 -2-F                 110 CH.sub.3 4-OC.sub.2 H.sub.5 C(=O)OC.sub.2 H.sub.5                         111 CH.sub.3 4-OC.sub.2 H.sub.5 C(=O)NHCH.sub.3                               112 CH.sub.3 4-OC.sub.2 H.sub.5 C(=O)C(=O)OC.sub.2 H.sub.5                    113 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.3                                   114 CH.sub.3 4-O-n-C.sub.3 H.sub.7 C.sub.2 H.sub.5                            115 CH.sub.3 4-O-n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7                          116 CH.sub.3 4-O-n-C.sub.3 H.sub.7 i-C.sub.3 H.sub.7                          117 CH.sub.3 4-O-n-C.sub.3 H.sub.7 n-C.sub.4 H.sub.9                          118 CH.sub.3 4-O-n-C.sub.3 H.sub.7 n-C.sub.6 H.sub.13                         119 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 F                                 120 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CHF.sub.2                                  121 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 CF.sub.3                          122 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 CH=CH.sub.2                       123 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 CH=CHCH.sub.3                     124 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 CH=C(CH.sub.3).sub.2                                            125 CH.sub.3 4-O-n-C.sub.3 H.sub.7                                           CH.sub.2 CH=CHCl                                 126 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 CH=CCl.sub.2                      127 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 C(CH.sub.3)=CH.sub.2                                            128 CH.sub.3 4-O-n-C.sub.3 H.sub.7                                           CH.sub.2 C=CH                                    129 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 Si(CH.sub.3).sub.3                130 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 -c.propyl-2,2-Cl.sub.2                                          131 CH.sub.3 4-O-n-C.sub.3 H.sub.7                                           CH.sub.2 CN                                      132 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 COOC.sub.2 H.sub.5                133 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH(CH.sub.3)COOC.sub.2 H.sub.5                                           134 CH.sub.3 4-O-n-C.sub.3 H.sub.7                                           CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3                                           135 CH.sub.3 4-O-n-C.sub.3 H.sub.7                                           CH.sub.2 C.sub.6 H.sub.4 -4-F                    136 CH.sub.3 4-O-n-C.sub.3 H.sub.7 CH.sub.2 C.sub.6 H.sub.4 -3-F                                            137 CH.sub.3 4-O-n-C.sub.3 H.sub.7                                           CH.sub.2 C.sub.6 H.sub.4 -2-F                    138 CH.sub.3 4-O-n-C.sub.3 H.sub.7 C(=O)OC.sub.2 H.sub.5                      139 CH.sub.3 4-O-n-C.sub.3 H.sub.7 C(=O)NHCH.sub.3                            140 CH.sub.3 4-O-n-C.sub.3 H.sub.7 C(=O)C(=O)OC.sub.2 H.sub.5                 141 CH.sub.3 2-CH.sub.3 CH.sub.3                                              142 CH.sub.3 2-CH.sub.3 C.sub.2 H.sub.5                                       143 CH.sub.3 2-CH.sub.3 n-C.sub.3 H.sub.7                                     144 CH.sub.3 2-CH.sub.3 i-C.sub.3 H.sub.7                                     145 CH.sub.3 2-CH.sub.3 n-C.sub.4 H.sub.9                                     146 CH.sub.3 2-CH.sub.3 n-C.sub.6 H.sub.13                                    147 CH.sub.3 2-CH.sub.3 CH.sub.2 F                                            148 CH.sub.3 2-CH.sub.3 CHF.sub.2                                             149 CH.sub.3 2-CH.sub.3 CH.sub.2 CF.sub.3                                     150 CH.sub.3 2-CH.sub.3 CH.sub.2 CH=CH.sub.2                                  151 CH.sub.3 2-CH.sub.3 CH.sub.2 CH=CHCH.sub.3                                152 CH.sub.3 2-CH.sub.3 CH.sub.2 CH=C(CH.sub.3).sub.2                         153 CH.sub.3 2-CH.sub.3 CH.sub.2 CH=CHCl                                      154 CH.sub.3 2-CH.sub.3 CH.sub.2 CH=CCl.sub.2                                 155 CH.sub.3 2-CH.sub.3 CH.sub.2 C(CH.sub.3)=CH.sub.2                         156 CH.sub.3 2-CH.sub.3 CH.sub.2 C=CH                                         157 CH.sub.3 2-CH.sub.3 CH.sub.2 Si(CH.sub.3).sub.3                           158 CH.sub.3 2-CH.sub.3 CH.sub.2 -c.propyl-2,2-Cl.sub.2                       159 CH.sub.3 2-CH.sub.3 CH.sub.2 CN                                           160 CH.sub.3 2-CH.sub.3 CH.sub.2 COOC.sub.2 H.sub.5                           161 CH.sub.3 2-CH.sub.3 CH(CH.sub.3)COOC.sub.2 H.sub.5                        162 CH.sub.3 2-CH.sub.3 CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3                  163 CH.sub.3 2-CH.sub.3 CH.sub.2 C.sub.6 H.sub.4 -4-F                         164 CH.sub.3 2-CH.sub.3 CH.sub.2 C.sub.6 H.sub.4 -3-F                         165 CH.sub.3 2-CH.sub.3 CH.sub.2 C.sub.6 H.sub.4 -2-F                         166 CH.sub.3 2-CH.sub.3 C(=O)OC.sub.2 H.sub.5                                 167 CH.sub.3 2-CH.sub.3 C(=O)NHCH.sub.3                                       168 CH.sub.3 2-CH.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5                            169 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.3                          170 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 C.sub.2 H.sub.5                   171 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 n-C.sub.3 H.sub.7                 172 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 i-C.sub.3 H.sub.7                 173 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 n-C.sub.4 H.sub.9                 174 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 n-C.sub.6 H.sub.13                175 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 F                        176 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CHF.sub.2                         177 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 CF.sub.3                 178 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 CH=CH.sub.2                                            179 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.                                   3 CH.sub.2 CH=CHCH.sub.3                         180 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 CH=C(CH.sub.3).sub.                                   2                                                181 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 CH=CHCl                  182 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 CH=CCl.sub.2                                           183 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.                                   3 CH.sub.2 C(CH.sub.3)=CH.sub.2                  184 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 C=CH                     185 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 Si(CH.sub.3).sub.3       186 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 -c.propyl-2,2-Cl.su                                   b.2                                              187 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 CN                       188 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 COOC.sub.2 H.sub.5       189 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH(CH.sub.3)COOC.sub.2                                         H.sub.5                                          190 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -3-CF.sub.3                                      191 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -4-F                                             192 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -3-F                                             193 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -2-F                                             194 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 C(=O)OC.sub.2 H.sub.5                                           195 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.                                   3 C(=O)NHCH.sub.3                                196 CH.sub.3 4-OCH.sub.2 Si(CH.sub.3).sub.3 C(=O)C(=O)OC.sub.2 H.sub.5                                      197 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 CH.sub.3                             198 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 C.sub.2 H.sub.5                                        199 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 n-C.sub.3 H.sub.7                    200 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 i-C.sub.3 H.sub.7                                      201 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 n-C.sub.4 H.sub.9                    202 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 n-C.sub.6 H.sub.13       203 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 F                                             204 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 CHF.sub.2                            205 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CF.sub.3                                      206 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 CH.sub.2 CH=CH.sub.2                 207 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CH=CHCH.su                                   b.3                                              208 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CH=C(CH.su                                   b.3).sub.2                                       209 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CH=CHCl                                       210 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 CH.sub.2 CH=CCl.sub.2                211 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C(CH.sub.3                                   )=CH.sub.2                                       212 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C=CH                                          213 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 CH.sub.2 Si(CH.sub.3).sub.3                                        214 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 CH.sub.2 -c.propyl-2,2-Cl.sub.2      215 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CN                                            216 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 CH.sub.2 COOC.sub.2 H.sub.5                                        217 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 CH(CH.sub.3)COOC.sub.2 H.sub.5       218 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -3-CF.sub.3                              219 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -4-F                                     220 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -3-F                                     221 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -2-F                                     222 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 C(=O)OC.sub.2                                         H.sub.5                                          223 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3 C(=O)NHCH.sub.3                                        224 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-CF.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5                                         225 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 CH.sub.3                             226 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 C.sub.2 H.sub.5                                        227 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 n-C.sub.3 H.sub.7                    228 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 i-C.sub.3 H.sub.7                                      229 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 n-C.sub.4 H.sub.9                    230 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 n-C.sub.6 H.sub.13       231 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 F                                             232 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 CHF.sub.2                            233 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 CF.sub.3                                      234 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 CH.sub.2 CH=CH.sub.2                 235 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 CH=CHCH.su                                   b.3                                              236 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 CH=C(CH.su                                   b.3).sub.2                                       237 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 CH=CHCl                                       238 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 CH.sub.2 CH=CCl.sub.2                239 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 C(CH.sub.3                                   )=CH.sub.2                                       240 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 C=CH                                          241 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 CH.sub.2 Si(CH.sub.3).sub.3                                        242 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 CH.sub.2 -c.propyl-2,2-Cl.sub.2      243 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 CN                                            244 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 CH.sub.2 COOC.sub.2 H.sub.5                                        245 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 CH(CH.sub.3)COOC.sub.2 H.sub.5       246 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -3-CF.sub.3                              247 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -4-F                                     248 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -3-F                                     249 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -2-F                                     250 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 C(=O)OC.sub.2                                         H.sub.5                                          251 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 C(=O)NHCH.sub.3                                        252 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5                                         253 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 CH.sub.3                             254 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 C.sub.2 H.sub.5                                        255 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF3 n-C.sub.3 H.sub.7                         256 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 i-C.sub.3 H.sub.7                                      257 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 n-C.sub.4 H.sub.9                    258 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 n-C.sub.6 H.sub.13       259 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 F                                             260 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 CHF.sub.2                            261 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CF.sub.3                                      262 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 CH.sub.2 CH=CH.sub.2                 263 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CH=CHCH.su                                   b.3                                              264 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CH=C(CH.su                                   b.3).sub.2                                       265 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CH=CHCl                                       266 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 CH.sub.2 CH=CCl.sub.2                267 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C(CH.sub.3                                   )=CH.sub.2                                       268 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C=CH                                          269 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 CH.sub.2 Si(CH.sub.3).sub.3                                        270 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 CH.sub.2 -c.propyl-2,2-Cl.sub.2      271 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CN                                            272 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 CH.sub.2 COOC.sub.2 H.sub.5                                        273 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 CH(CH.sub.3)COOC.sub.2 H.sub.5       274 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -3-CF.sub.3                              275 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -4-F                                     276 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -3-F                                     277 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C.sub.6                                      H.sub.4 -2-F                                     278 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 C(=O)OC.sub.2                                         H.sub.5                                          279 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -2-CF.sub.3 C(=O)NHCH.sub.3                                        280 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -2-CF.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5                                         281 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-F CH.sub.3                                    282 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F C.sub.2 H.sub.5                 283 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F n-C.sub.3 H.sub.7                                             284 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-F i-C.sub.3 H.sub.7                           285 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F n-C.sub.4 H.sub.9                                             286 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-F n-C.sub.6 H.sub.13                          287 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 F                      288 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CHF.sub.2                       289 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 CF.sub.3                                             290 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-F CH.sub.2 CH=CH.sub.2                        291 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 CH=CHCH.sub.3                                        292 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-F CH.sub.2 CH=C(CH.sub.3).sub.2                                             293 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-F CH.sub.2 CH=CHCl                            294 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 CH=CCl.sub.2                                         295 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-F CH.sub.2 C(CH.sub.3)=CH.sub.2                                             296 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-F CH.sub.2 C=CH                               297 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 Si(CH.sub.3).sub.                                   3                                                298 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 -c.propyl-2,2-Cl.                                   sub.2                                            299 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 CN                     300 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 COOC.sub.2                                          H.sub.5                                          301 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH(CH.sub.3)COOC.sub.2                                       H.sub.5                                          302 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3                                      303 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 C.sub.6 H.sub.4                                     -4-F                                             304 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 C.sub.6 H.sub.4                                     -3-F                                             305 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F CH.sub.2 C.sub.6 H.sub.4                                     -2-F                                             306 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F C(=O)OC.sub.2 H.sub.5                                         307 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-F C(=O)NHCH.sub.3                             308 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-F C(=O)C(=O)OC.sub.2                                           H.sub.5                                          309 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.3                           310 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 C.sub.2 H.sub.5                    311 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 n-C.sub.3 H.sub.7                  312 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 i-C.sub.3 H.sub.7                  313 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 n-C.sub.4 H.sub.9                  314 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 n-C.sub.6 H.sub.13                 315 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 F                         316 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CHF.sub.2                          317 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 CF.sub.3                  318 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 CH=CH.sub.2                                             319 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3                                    CH.sub.2 CH=CHCH.sub.3                          320 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 CH=C(CH.sub.3).sub.2      321 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 CH=CHCl                   322 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 CH=CCl.sub.2                                            323 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3                                    CH.sub.2 C(CH.sub.3)=CH.sub.2                   324 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 C=CH                      325 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 Si(CH.sub.3).sub.3                                      326 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3                                    CH.sub.2 -c.propyl-2,2-Cl.sub.2                 327 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 CN                        328 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 COOC.sub.2 H.sub.5                                      329 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3                                    CH(CH.sub.3)COOC.sub.2 H.sub.5                  330 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                        -3-CF.sub.3                                      331 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                        -4-F                                             332 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                        -3-F                                             333 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                        -2-F                                             334 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 C(=O)OC.sub.2 H.sub.5                                            335 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3                                    C(=O)NHCH.sub.3                                 336 CH.sub.3 4-OC.sub.6 H.sub.4 3-CF.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5                                       337 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6                                      H.sub.4 -3-CF.sub.3 CH.sub.3                     338 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 C.sub.2                                        H.sub.5                                          339 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 n-C.sub.3                                      H.sub.7                                          340 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 i-C.sub.3                                      H.sub.7                                          341 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 n-C.sub.4                                      H.sub.9                                          342 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 n-C.sub.6                                      H.sub.13                                         343 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 F                                      344 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6                                      H.sub.4 -3-CF.sub.3 CHF.sub.2                    345 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       CF.sub.3                                         346 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       CH=CH.sub.2                                      347 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       CH=CHCH.sub.3                                    348 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       CH=C(CH.sub.3).sub.2                             349 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       CH=CHCl                                          350 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       CH=CCl.sub.2                                     351 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       C(CH.sub.3)=CH.sub.2                             352 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       C=CH                                             353 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       Si(CH.sub.3).sub.3                               354 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       -c.propyl-2,2-Cl.sub.2                           355 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2 CN       356 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       COOC.sub.2 H.sub.5                               357 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH(CH.sub.3)                                   COOC.sub.2 H.sub.5                               358 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       C.sub.6 H.sub.4 -3-CF.sub.3                      359 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       C.sub.6 H.sub.4 -4-F                             360 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       C.sub.6 H.sub.4 -3-F                             361 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 CH.sub.2                                       C.sub.6 H.sub.4 -2-F                             362 C.sub.2 H.sub.5 4-OC.sub.6 H.sub.4 -3-CF.sub.3 C(=O)OC.sub.2                                           H.sub.5                                          363 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 C(=O)NHCH.su                                   b.3                                              364 C.sub.2 H.sub.5 4-OCH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.3 C(=O)C(=O)OC                                   .sub.2 H.sub.5                                   365 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.3                                366 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl C.sub.2 H.sub.5                         367 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl n-C.sub.3 H.sub.7                       368 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl i-C.sub.3 H.sub.7                       369 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl n-C.sub.4 H.sub.9                       370 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl n-C.sub.6 H.sub.13                      371 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 F                              372 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CHF.sub.2                               373 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 CF.sub.3                       374 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 CH=CH.sub.2                    375 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 CH=CHCH.sub.3                  376 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 CH=C(CH.sub.3).sub.2                                         377 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl                                        CH.sub.2 CH=CHCl                                 378 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 CH=CCl.sub.2                   379 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 C(CH.sub.3)=CH.sub.2                                         380 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl                                        CH.sub.2 C=CH                                    381 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 Si(CH.sub.3).sub.3                                           382 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl                                        CH.sub.2 -c.propyl-2,2-Cl.sub.2                  383 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 CN                             384 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 COOC.sub.2 H.sub.5                                           385 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl                                        CH(CH.sub.3)COOC.sub.2 H.sub.5                   386 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub                                   .3                                               387 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 C.sub.6 H.sub.4 -4-F                                         388 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl                                        CH.sub.2 C.sub.6 H.sub.4 -3-F                    389 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl CH.sub.2 C.sub.6 H.sub.4 -2-F                                         390 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl                                        C(=O)OC.sub.2 H.sub.5                            391 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl C(=O)NHCH.sub.3                         392 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Cl C(=O)C(=O)OC.sub.2 H.sub.5                                            393 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl                                        CH.sub.3                                         394 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl C.sub.2 H.sub.5                         395 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl n-C.sub.3 H.sub.7                       396 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl i-C.sub.3 H.sub.7                       397 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl n-C.sub.4 H.sub.9                       398 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl n-C.sub.6 H.sub.13                      399 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 F                              400 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CHF.sub.2                               401 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 CF.sub.3                       402 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 CH=CH.sub.2                    403 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 CH=CHCH.sub.3                  404 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 CH=C(CH.sub.3).sub.2                                         405 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl                                        CH.sub.2 CH=CHCl                                 406 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 CH=CCl.sub.2                   407 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 C(CH.sub.3)=CH.sub.2                                         408 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl                                        CH.sub.2 C=CH                                    409 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 Si(CH.sub.3).sub.3                                           410 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl                                        CH.sub.2 -c.propyl-2,2-Cl.sub.2                  411 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 CN                             412 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 COOC.sub.2 H.sub.5                                           413 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl                                        CH(CH.sub.3)COOC.sub.2 H.sub.5                   414 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub                                   .3                                               415 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 C.sub.6 H.sub.4 -4-F                                         416 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl                                        CH.sub.2 C.sub.6 H.sub.4 -3-F                    417 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl CH.sub.2 C.sub.6 H.sub.4 -2-F                                         418 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl                                        C(=O)OC.sub.2 H.sub.5                            419 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl C(=O)NHCH.sub.3                         420 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Cl C(=O)C(=O)OC.sub.2 H.sub.5                                            421 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl                                        CH.sub.3                                         422 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl C.sub.2 H.sub.5                         423 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl n-C.sub.3 H.sub.7                       424 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl i-C.sub.3 H.sub.7                       425 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl n-C.sub.4 H.sub.9                       426 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl n-C.sub.6 H.sub.13                      427 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 F                              428 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CHF.sub.2                               429 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 CF.sub.3                       430 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 CH=CH.sub.2                    431 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 CH=CHCH.sub.3                  432 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 CH=C(CH.sub.3).sub.2                                         433 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl                                        CH.sub.2 CH=CHCl                                 434 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 CH=CCl.sub.2                   435 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 C(CH.sub.3)=CH.sub.2                                         436 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl                                        CH.sub.2 C=CH                                    437 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 Si(CH.sub.3).sub.3                                           438 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl                                        CH.sub.2 -c.propyl-2,2-Cl.sub.2                  439 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 CN                             440 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 COOC.sub.2 H.sub.5                                           441 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl                                        CH(CH.sub.3)COOC.sub.2 H.sub.5                   442 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub                                   .3                                               443 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 C.sub.6 H.sub.4 -4-F                                         444 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl                                        CH.sub.2 C.sub.6 H.sub.4 -3-F                    445 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl CH.sub.2 C.sub.6 H.sub.4 -2-F                                         446 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl                                        C(=O)OC.sub.2 H.sub.5                            447 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl C(=O)NHCH.sub.3                         448 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Cl C(=O)C(=O)OC.sub.2 H.sub.5                                            449 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F                                         CH.sub.3                                         450 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F C.sub.2 H.sub.5                          451 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F n-C.sub.3 H.sub.7                        452 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F i-C.sub.3 H.sub.7                        453 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F n-C.sub.4 H.sub.9                        454 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F n-C.sub.6 H.sub.13                       455 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 F                               456 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CHF.sub.2                                457 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 CF.sub.3                        458 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 CH=CH.sub.2                     459 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 CH=CHCH.sub.3                   460 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 CH=C(CH.sub.3).sub.2                                          461 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F                                         CH.sub.2 CH=CHCl                                 462 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 CH=CCl.sub.2                    463 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 C(CH.sub.3)=CH.sub.2                                          464 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F                                         CH.sub.2 C=CH                                    465 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 Si(CH.sub.3).sub.3                                            466 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F                                         CH.sub.2 -c.propyl-2,2-Cl.sub.2                  467 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 CN                              468 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 COOC.sub.2 H.sub.5                                            469 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F                                         CH(CH.sub.3)COOC.sub.2 H.sub.5                   470 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.                                   3                                                471 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 C.sub.6 H.sub.4 -4-F                                          472 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F                                         CH.sub.2 C.sub.6 H.sub.4 -3-F                    473 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F CH.sub.2 C.sub.6 H.sub.4 -2-F                                          474 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F                                         C(=O)OC.sub.2 H.sub.5                            475 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F C(=O)NHCH.sub.3                          476 CH.sub.3 4-OC.sub.6 H.sub.4 -4-F C(=O)C(=O)OC.sub.2 H.sub.5                                             477 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F                                         CH.sub.3                                         478 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F C.sub.2 H.sub.5                          479 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F n-C.sub.3 H.sub.7                        480 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F i-C.sub.3 H.sub.7                        481 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F n-C.sub.4 H.sub.9                        482 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F n-C.sub.6 H.sub.13                       483 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 F                               484 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CHF.sub.2                                485 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 CF.sub.3                        486 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 CH=CH.sub.2                     487 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 CH=CHCH.sub.3                   488 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 CH=C(CH.sub.3).sub.2                                          489 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F                                         CH.sub.2 CH=CHCl                                 490 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 CH=CCl.sub.2                    491 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 C(CH.sub.3)=CH.sub.2                                          492 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F                                         CH.sub.2 C=CH                                    493 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 Si(CH.sub.3).sub.3                                            494 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F                                         CH.sub.2 -c.propyl-2,2-Cl.sub.2                  495 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 CN                              496 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 COOC.sub.2 H.sub.5                                            497 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F                                         CH(CH.sub.3)COOC.sub.2 H.sub.5                   498 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.                                   3                                                499 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 C.sub.6 H.sub.4 -4-F                                          500 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F                                         CH.sub.2 C.sub.6 H.sub.4 -3-F                    501 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F CH.sub.2 C.sub.6 H.sub.4 -2-F                                          502 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F                                         C(=O)OC.sub.2 H.sub.5                            503 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F C(=O)NHCH.sub.3                          504 CH.sub.3 4-OC.sub.6 H.sub.4 -3-F C(=O)C(=O)OC.sub.2 H.sub.5                                             505 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F                                         CH.sub.3                                         506 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F C.sub.2 H.sub.5                          507 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F n-C.sub.3 H.sub.7                        508 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F i-C.sub.3 H.sub.7                        509 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F n-C.sub.4 H.sub.9                        510 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F n-C.sub.6 H.sub.13                       511 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 F                               512 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CHF.sub.2                                513 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 CF.sub.3                        514 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 CH=CH.sub.2                     515 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 CH=CHCH.sub.3                   516 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 CH=C(CH.sub.3).sub.2                                          517 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F                                         CH.sub.2 CH=CHCl                                 518 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 CH=CCl.sub.2                    519 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 C(CH.sub.3)=CH.sub.2                                          520 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F                                         CH.sub.2 C=CH                                    521 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 Si(CH.sub.3).sub.3                                            522 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F                                         CH.sub.2 -c.propyl-2,2-Cl.sub.2                  523 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 CN                              524 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 COOC.sub.2 H.sub.5                                            525 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F                                         CH(CH.sub.3)COOC.sub.2 H.sub.5                   526 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub.                                   3                                                527 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 C.sub.6 H.sub.4 -4-F                                          528 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F                                         CH.sub.2 C.sub.6 H.sub.4 -3-F                    529 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F CH.sub.2 C.sub.6 H.sub.4 -2-F                                          530 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F                                         C(=O)OC.sub.2 H.sub.5                            531 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F C(=O)NHCH.sub.3                          532 CH.sub.3 4-OC.sub.6 H.sub.4 -2-F C(=O)C(=O)OC.sub.2 H.sub.5                                             533 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br                                        CH.sub.3                                         534 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br C.sub.2 H.sub.5                         535 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br n-C.sub.3 H.sub.7                       536 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br i-C.sub.3 H.sub.7                       537 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br n-C.sub.4 H.sub.9                       538 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br n-C.sub.6 H.sub.13                      539 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 F                              540 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CHF.sub.2                               541 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 CF.sub.3                       542 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 CH=CH.sub.2                    543 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 CH=CHCH.sub.3                  544 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 CH=C(CH.sub.3).sub.2                                         545 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br                                        CH.sub.2 CH=CHCl                                 546 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 CH=CCl.sub.2                   547 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 C(CH.sub.3)=CH.sub.2                                         548 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br                                        CH.sub.2 C=CH                                    549 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 Si(CH.sub.3).sub.3                                           550 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br                                        CH.sub.2 -c.propyl-2,2-Cl.sub.2                  551 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 CN                             552 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 COOC.sub.2 H.sub.5                                           553 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br                                        CH(CH.sub.3)COOC.sub.2 H.sub.5                   554 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub                                   .3                                               555 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 C.sub.6 H.sub.4 -4-F                                         556 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br                                        CH.sub.2 C.sub.6 H.sub.4 -3-F                    557 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br CH.sub.2 C.sub.6 H.sub.4 -2-F                                         558 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br                                        C(=O)OC.sub.2 H.sub.5                            559 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br C(=O)NHCH.sub.3                         560 CH.sub.3 4-OC.sub.6 H.sub.4 -4-Br C(=O)C(=O)OC.sub.2 H.sub.5                                            561 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br                                        CH.sub.3                                         562 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br C.sub.2 H.sub.5                         563 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br n-C.sub.3 H.sub.7                       564 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br i-C.sub.3 H.sub.7                       565 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br n-C.sub.4 H.sub.9                       566 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br n-C.sub.6 H.sub.13                      567 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 F                              568 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CHF.sub.2                               569 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 CF.sub.3                       570 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 CH=CH.sub.2                    571 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 CH=CHCH.sub.3                  572 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 CH=C(CH.sub.3).sub.2                                         573 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br                                        CH.sub.2 CH=CHCl                                 574 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 CH=CCl.sub.2                   575 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 C(CH.sub.3)=CH.sub.2                                         576 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br                                        CH.sub.2 C=CH                                    577 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 Si(CH.sub.3).sub.3                                           578 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br                                        CH.sub.2 -c.propyl-2,2-Cl.sub.2                  579 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 CN                             580 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 COOC.sub.2 H.sub.5                                           581 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br                                        CH(CH.sub.3)COOC.sub.2 H.sub.5                   582 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub                                   .3                                               583 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 C.sub.6 H.sub.4 -4-F                                         584 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br                                        CH.sub.2 C.sub.6 H.sub.4 -3-F                    585 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br CH.sub.2 C.sub.6 H.sub.4 -2-F                                         586 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br                                        C(=O)OC.sub.2 H.sub.5                            587 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br C(=O)NHCH.sub.3                         588 CH.sub.3 4-OC.sub.6 H.sub.4 -3-Br C(=O)C(=O)OC.sub.2 H.sub.5                                            589 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br                                        CH.sub.3                                         590 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br C.sub.2 H.sub.5                         591 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br n-C.sub.3 H.sub.7                       592 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br i-C.sub.3 H.sub.7                       593 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br n-C.sub.4 H.sub.9                       594 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br n-C.sub.6 H.sub.13                      595 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 F                              596 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CHF.sub.2                               597 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 CF.sub.3                       598 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 CH=CH.sub.2                    599 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 CH=CHCH.sub.3                  600 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 CH=C(CH.sub.3).sub.2                                         601 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br                                        CH.sub.2 CH=CHCl                                 602 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 CH=CCl.sub.2                   603 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 C(CH.sub.3)=CH.sub.2                                         604 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br                                        CH.sub.2 C=CH                                    605 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 Si(CH.sub.3).sub.3                                           606 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br                                        CH.sub.2 -c.propyl-2,2-Cl.sub.2                  607 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 CN                             608 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 COOC.sub.2 H.sub.5                                           609 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br                                        CH(CH.sub.3)COOC.sub.2 H.sub.5                   610 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 C.sub.6 H.sub.4 -3-CF.sub                                   .3                                               611 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 C.sub.6 H.sub.4 -4-F                                         612 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br                                        CH.sub.2 C.sub.6 H.sub.4 -3-F                    613 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br CH.sub.2 C.sub.6 H.sub.4 -2-F                                         614 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br                                        C(=O)OC.sub.2 H.sub.5                            615 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br C(=O)NHCH.sub.3                         616 CH.sub.3 4-OC.sub.6 H.sub.4 -2-Br C(=O)C(=O)OC.sub.2 H.sub.5                                            617 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.su                                   b.2 CH.sub.3                                     618 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 C.sub.2 H.sub.5                 619 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 n-C.sub.3 H.sub.7                                             620 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.su                                   b.2 i-C.sub.3 H.sub.7                            621 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 n-C.sub.4 H.sub.9                                             622 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.su                                   b.2 n-C.sub.6 H.sub.13                           623 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 F                      624 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CHF.sub.2                       625 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 CF.sub.3                                             626 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.su                                   b.2 CH.sub.2 CH=CH.sub.2                         627 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 CH=CHCH.sub.3                                        628 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.su                                   b.2 CH.sub.2 CH=C(CH.sub.3).sub.2                629 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 CH=CHCl                630 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 CH=CCl.sub.2                                         631 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.su                                   b.2 CH.sub.2 C(CH.sub.3)=CH.sub.2                632 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 C=CH                   633 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 Si(CH.sub.3).sub.                                   3                                                634 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 -c.propyl-2,2-Cl.                                   sub.2                                            635 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 CN                     636 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 COOC.sub.2                                          H.sub.5                                          637 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH(CH.sub.3)COOC.sub.2                                       H.sub.5                                          638 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3                                      639 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 C.sub.6 H.sub.4                                     -4-F                                             640 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 C.sub.6 H.sub.4                                     -3-F                                             641 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 CH.sub.2 C.sub.6 H.sub.4                                     -2-F                                             642 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 C(=O)OC.sub.2 H.sub.5                                         643 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.su                                   b.2 C(=O)NHCH.sub.3                              644 CH.sub.3 4-OC.sub.6 H.sub.3 -2,4-Cl.sub.2 C(=O)C(=O)OC.sub.2                                           H.sub.5                                          645 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.3                        646 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 C.sub.2 H.sub.5                 647 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 n-C.sub.3 H.sub.7                                             648 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.su                                   b.2 i-C.sub.3 H.sub.7                            649 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 n-C.sub.4 H.sub.9                                             650 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.su                                   b.2 n-C.sub.6 H.sub.13                           651 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 F                      652 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CHF.sub.2                       653 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 CF.sub.3                                             654 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.su                                   b.2 CH.sub.2 CH=CH.sub.2                         655 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 CH=CHCH.sub.3                                        656 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.su                                   b.2 CH.sub.2 CH=C(CH.sub.3).sub.2                657 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 CH=CHCl                658 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 CH=CCl.sub.2                                         659 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.su                                   b.2 CH.sub.2 C(CH.sub.3)=CH.sub.2                660 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C=CH                   661 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 Si(CH.sub.3).sub.                                   3                                                662 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 -c.propyl-2,2-Cl.                                   sub.2                                            663 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 CN                     664 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 COOC.sub.2                                          H.sub.5                                          665 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH(CH.sub.3)COOC.sub.2                                       H.sub.5                                          666 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C.sub.6 H.sub.4                                     -3-CF.sub.3                                      667 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C.sub.6 H.sub.4                                     -4-F                                             668 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C.sub.6 H.sub.4                                     -3-F                                             669 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C.sub.6 H.sub.4                                     -2-F                                             670 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 C(=O)OC.sub.2 H.sub.5                                         671 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.su                                   b.2 C(=O)NHCH.sub.3                              672 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-Cl.sub.2 C(=O)C(=O)OC.sub.2                                           H.sub.5                                          673 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.3                           674 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br C.sub.2 H.sub.5                    675 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br n-C.sub.3 H.sub.7                  676 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br i-C.sub.3 H.sub.7                  677 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br n-C.sub.4 H.sub.9                  678 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br n-C.sub.6 H.sub.13                 679 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 F                         680 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CHF.sub.2                          681 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 CF.sub.3                  682 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 CH=CH.sub.2                                             683 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br                                    CH.sub.2 CH=CHCH.sub.3                          684 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 CH=C(CH.sub.3).sub.2      685 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 CH=CHCl                   686 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 CH=CCl.sub.2                                            687 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br                                    CH.sub.2 C(CH.sub.3)=CH.sub.2                   688 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 C=CH                      689 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 Si(CH.sub.3).sub.3                                      690 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br                                    CH.sub.2 -c.propyl-2,2-Cl.sub.2                 691 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 CN                        692 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 COOC.sub.2 H.sub.5                                      693 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br                                    CH(CH.sub.3)COOC.sub.2 H.sub.5                  694 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 C.sub.6 H.sub.4                                        -3-CF.sub.3                                      695 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 C.sub.6 H.sub.4                                        -4-F                                             696 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 C.sub.6 H.sub.4                                        -3-F                                             697 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br CH.sub.2 C.sub.6 H.sub.4                                        -2-F                                             698 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br C(=O)OC.sub.2 H.sub.5                                            699 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br                                    C(=O)NHCH.sub.3                                 700 CH.sub.3 4-OC.sub.6 H.sub.3 -2-Cl,4-Br C(=O)C(=O)OC.sub.2 H.sub.5                                       701 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) CH.sub.3                               702 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) C.sub.2 H.sub.5                                         703 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) n-C.sub.3 H.sub.7                      704 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) i-C.sub.3 H.sub.7                                       705 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) n-C.sub.4 H.sub.9                      706 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) n-C.sub.6 H.sub.13                                      707 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) CH.sub.2 F                             708 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CHF.sub.2                 709 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 CF.sub.3                                       710 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) CH.sub.2 CH=CH.sub.2                   711 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 CH=CHCH.sub                                   .3                                               712 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 CH=C(CH.sub                                   .3).sub.2                                        713 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 CH=CHCl                                        714 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) CH.sub.2 CH=CCl.sub.2                  715 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 C(CH.sub.3)                                   =CH.sub.2                                        716 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 C=CH                                           717 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) CH.sub.2 Si(CH.sub.3).sub.3                                          718 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) CH.sub.2 -c.propyl-2,2-Cl.sub.2                                      719 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) CH.sub.2 CN                            720 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 COOC.sub.2                                    H.sub.5                                          721 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH(CH.sub.3)COOC.sub                                   .2 H.sub.5                                       722 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 C.sub.6                                       H.sub.4 -3-CF.sub.3                              723 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 C.sub.6                                       H.sub.4 -4-F                                     724 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 C.sub.6                                       H.sub.4 -3-F                                     725 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) CH.sub.2 C.sub.6                                       H.sub.4 -2-F                                     726 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) C(=O)OC.sub.2                                          H.sub.5                                          727 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.sub.2 O-) C(=O)NHCH.sub.3                                         728 CH.sub.3 4-OC.sub.6 H.sub.3 -3,4-(-CH.                                   sub.2 O-) C(=O)C(=O)OC.sub.2 H.sub.5                                           729 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub                                   .3 CH.sub.3                                      730 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 C.sub.2 H.sub.5                  731 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 n-C.sub.3 H.sub.7                732 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 i-C.sub.3 H.sub.7                733 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 n-C.sub.4 H.sub.9                734 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 n-C.sub.6 H.sub.13                                             735 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub                                   .3 CH.sub.2 F                                    736 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CHF.sub.2                        737 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 CF.sub.3                738 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 CH=CH.sub.2                                           739 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub                                   .3 CH.sub.2 CH=CHCH.sub.3                        740 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 CH=C(CH.sub.3).sub                                   .2                                               741 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 CH=CHCl                 742 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 CH=CCl.sub.2                                          743 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub                                   .3 CH.sub.2 C(CH.sub.3)=CH.sub.2                 744 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 C=CH                    745 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 Si(CH.sub.3).sub.3      746 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 -c.propyl-2,2-Cl.s                                   ub.2                                             747 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 CN                      748 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 COOC.sub.2                                           H.sub.5                                          749 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH(CH.sub.3)COOC.sub.2                                        H.sub.5                                          750 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 C.sub.6 H.sub.4                                      -3-CF.sub.3                                      751 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 C.sub.6 H.sub.4                                      -4-F                                             752 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 C.sub.6 H.sub.4                                      -3-F                                             753 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 CH.sub.2 C.sub.6 H.sub.4                                      -2-F                                             754 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 C(=O)OC.sub.2 H.sub.5                                          755 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub                                   .3 C(=O)NHCH.sub.3                               756 CH.sub.3 4-OC.sub.6 H.sub.4 -4-SCH.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5       757 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.3                         758 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 C.sub.2 H.sub.5                  759 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 n-C.sub.3 H.sub.7                760 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 i-C.sub.3 H.sub.7                761 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 n-C.sub.4 H.sub.9                762 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 n-C.sub.6 H.sub.13                                             763 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub                                   .3 CH.sub.2 F                                    764 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CHF.sub.2                        765 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 CF.sub.3                766 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 CH=CH.sub.2                                           767 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub                                   .3 CH.sub.2 CH=CHCH.sub.3                        768 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 CH=C(CH.sub.3).sub                                   .2                                               769 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 CH=CHCl                 770 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 CH=CCl.sub.2                                          771 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub                                   .3 CH.sub.2 C(CH.sub.3)=CH.sub.2                 772 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 C=CH                    773 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 Si(CH.sub.3).sub.3      774 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 -c.propyl-2,2-Cl.s                                   ub.2                                             775 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 CN                      776 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 COOC.sub.2                                           H.sub.5                                          777 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH(CH.sub.3)COOC.sub.2                                        H.sub.5                                          778 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 C.sub.6 H.sub.4                                      -3-CF.sub.3                                      779 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 C.sub.6 H.sub.4                                      -4-F                                             780 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 C.sub.6 H.sub.4                                      -3-F                                             781 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 CH.sub.2 C.sub.6 H.sub.4                                      -2-F                                             782 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 C(=O)OC.sub.2 H.sub.5                                          783 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub                                   .3 C(=O)NHCH.sub.3                               784 CH.sub.3 4-OC.sub.6 H.sub.4 -4-OCH.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5       785 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.3                           786 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl C.sub.2 H.sub.5                    787 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl n-C.sub.3 H.sub.7                  788 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl i-C.sub.3 H.sub.7                  789 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl n-C.sub.4 H.sub.9                  790 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl n-C.sub.6 H.sub.13                 791 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 F                         792 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CHF.sub.2                          793 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 CF.sub.3                  794 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 CH=CH.sub.2                                             795 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl                                    CH.sub.2 CH=CHCH.sub.3                          796 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 CH=C(CH.sub.3).sub.2      797 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 CH=CHCl                   798 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 CH=CCl.sub.2                                            799 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl                                    CH.sub.2 C(CH.sub.3)=CH.sub.2                   800 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 C=CH                      801 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 Si(CH.sub.3).sub.3                                      802 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl                                    CH.sub.2 -c.propyl-2,2-Cl.sub.2                 803 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 CN                        804 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 COOC.sub.2 H.sub.5                                      805 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl                                    CH(CH.sub.3)COOC.sub.2 H.sub.5                  806 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 C.sub.6 H.sub.4                                        -3-CF.sub.3                                      807 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 C.sub.6 H.sub.4                                        -4-F                                             808 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 C.sub.6 H.sub.4                                        -3-F                                             809 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl CH.sub.2 C.sub.6 H.sub.4                                        -2-F                                             810 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl C(=O)OC.sub.2 H.sub.5                                            811 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl                                    C(=O)NHCH.sub.3                                 812 CH.sub.3 4-OC.sub.6 H.sub.4 -4-t-butyl C(=O)C(=O)OC.sub.2 H.sub.5                                       813 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.                                   3 CH.sub.3                                       814 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 C.sub.2 H.sub.5                   815 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 n-C.sub.3 H.sub.7                 816 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 i-C.sub.3 H.sub.7                 817 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 n-C.sub.4 H.sub.9                 818 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 n-C.sub.6 H.sub.13                819 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 F                        820 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CHF.sub.2                         821 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CF.sub.3                 822 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CH=CH.sub.2                                            823 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.                                   3 CH.sub.2 CH=CHCH.sub.3                         824 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CH=C(CH.sub.3).sub.                                   2                                                825 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CH=CHCl                  826 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CH=CCl.sub.2                                           827 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.                                   3 CH.sub.2 C(CH.sub.3)=CH.sub.2                  828 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C=CH                     829 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 Si(CH.sub.3).sub.3       830 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 -c.propyl-2,2-Cl.su                                   b.2                                              831 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 CN                       832 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 COOC.sub.2 H.sub.5       833 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH(CH.sub.3)COOC.sub.2                                         H.sub.5                                          834 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -3-CF.sub.3                                      835 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -4-F                                             836 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -3-F                                             837 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -2-F                                             838 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 C(=O)OC.sub.2 H.sub.5                                           839 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.                                   3 C(=O)NHCH.sub.3                                840 CH.sub.3 4-OC.sub.6 H.sub.4 -4-CF.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5                                      841 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.                                   3 CH.sub.3                                       842 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 C.sub.2 H.sub.5                   843 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 n-C.sub.3 H.sub.7                 844 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 i-C.sub.3 H.sub.7                 845 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 n-C.sub.4 H.sub.9                 846 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 n-C.sub.6 H.sub.13                847 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 F                        848 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CHF.sub.2                         849 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CF.sub.3                 850 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CH=CH.sub.2                                            851 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.                                   3 CH.sub.2 CH=CHCH.sub.3                         852 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CH=C(CH.sub.3).sub.                                   2                                                853 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CH=CHCl                  854 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CH=CCl.sub.2                                           855 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.                                   3 CH.sub.2 C(CH.sub.3)=CH.sub.2                  856 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C=CH                     857 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 Si(CH.sub.3).sub.3       858 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 -c.propyl-2,2-Cl.su                                   b.2                                              859 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 CN                       860 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 COOC.sub.2 H.sub.5       861 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH(CH.sub.3)COOC.sub.2                                         H.sub.5                                          862 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -3-CF.sub.3                                      863 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -4-F                                             864 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -3-F                                             865 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 CH.sub.2 C.sub.6 H.sub.4                                       -2-F                                             866 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 C(=O)OC.sub.2 H.sub.5                                           867 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.                                   3 C(=O)NHCH.sub.3                                868 CH.sub.3 4-OC.sub.6 H.sub.4 -2-CF.sub.3 C(=O)C(=O)OC.sub.2 H.sub.5                                      869 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-Cl CH.sub.3                                   870 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl C.sub.2 H.sub.5                871 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl n-C.sub.3 H.sub.7                                            872 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-Cl i-C.sub.3 H.sub.7                          873 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl n-C.sub.4 H.sub.9                                            874 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-Cl n-C.sub.6 H.sub.13                         875 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 F                     876 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CHF.sub.2                      877 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 CF.sub.3                                            878 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-Cl CH.sub.2 CH=CH.sub.2                       879 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 CH=CHCH.sub.3                                       880 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-Cl CH.sub.2 CH=C(CH.sub.3).sub.2                                            881 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-Cl CH.sub.2 CH=CHCl                           882 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 CH=CCl.sub.2                                        883 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-Cl CH.sub.2 C(CH.sub.3)=CH.sub.2                                            884 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-Cl CH.sub.2 C=CH                              885 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 Si(CH.sub.3).sub                                   .3                                               886 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 -c.propyl-2,2-Cl                                   .sub.2                                           887 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 CN                    888 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 COOC.sub.2                                         H.sub.5                                          889 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH(CH.sub.3)COOC.sub.2                                      H.sub.5                                          890 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 C.sub.6 H.sub.4                                    -3-CF.sub.3                                      891 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 C.sub.6 H.sub.4                                    -4-F                                             892 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 C.sub.6 H.sub.4                                    -3-F                                             893 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl CH.sub.2 C.sub.6 H.sub.4                                    -2-F                                             894 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl C(=O)OC.sub.2 H.sub.5                                        895 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4                                     -4-Cl C(=O)NHCH.sub.3                            896 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.4 -4-Cl C(=O)C(=O)OC.sub.2                                          H.sub.5                                          797 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.3                                             898 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3                                     -3,4-Cl.sub.2 C.sub.2 H.sub.5                    899 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 n-C.sub.3                                           H.sub.7                                          900 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 i-C.sub.3                                           H.sub.7                                          901 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 n-C.sub.4                                           H.sub.9                                          902 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 n-C.sub.6                                           H.sub.13                                         903 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 F                                           904 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3                                     -3,4-Cl.sub.2 CHF.sub.2                          905 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2                                            CF.sub.3                                         906 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2                                            CH=CH.sub.2                                      907 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2                                            CH=CHCH.sub.3                                    908 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2                                            CH=C(CH.sub.3).sub.2                             909 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 CH=CHCl       910 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2                                            CH=CCl.sub.2                                     911 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2                                            C(CH.sub.3)=CH.sub.2                             912 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C=CH                                        913 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3                                     -3,4-Cl.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                                      914 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3                                     -3,4-Cl.sub.2 CH.sub.2 -c.propyl-2,2-Cl.sub                                   .2                                               915 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 CN                                          916 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3                                     -3,4-Cl.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                                      917 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3                                     -3,4-Cl.sub.2 CH(CH.sub.3)COOC.sub.2                                          H.sub.5                                          918 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C.sub.6                                    H.sub.4 -3-CF.sub.3                              919 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C.sub.6                                    H.sub.4 -4-F                                     920 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C.sub.6                                    H.sub.4 -3-F                                     921 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 CH.sub.2 C.sub.6                                    H.sub.4 -2-F                                     922 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 C(=O)OC.sub.2                                       H.sub.5                                          923 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3 -3,4-Cl.sub.2 C(=O)NHCH.sub.3                                      924 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.3                                     -3,4-Cl.sub.2 C(=O)C(=O)OC.sub.2 H.sub.5       ______________________________________                                    

In Tables 2.1 and 2.2, the ¹³ C-NMR data of the compounds1-[4-(3-trifluoromethyl-phenylmethoxy)-phenyl]-1,2-propanedione1-E-[methyloxime]-2-oxime and1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-Z-[methyloxime]-2-oxime (which was prepared by one of the knownprocesses and from which the E/Z isomer mixture formed in thepreparation was isolated) or, respectively, methyl2-[[[(1-methyl-2-(4-(3-trifluoromethylphenylmethoxy)-phenyl)-2-E-[methoxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate(compound A225 in Table 1) are shown. The similar chemical shifts ofatoms 1 and 4 of compound A in Table 2.1 and those in Table 2.2 confirmthe E configuration of the compounds of the formula I.

                  TABLE 2.1                                                       ______________________________________                                        .sup.13 C-NMR shifts and .sup.1 J.sub.cc coupling constants of 1-[4-(3-        trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione                        1-E-[methyloxime]-2-oxime (A) and 1-[4-(3-                                    trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione                        1-Z-[methyloxime]-2-oxime (B)                                                ______________________________________                                          #STR10##                                                                      -                                                                             #STR11##                                                                      -                                                                             Compound  Atom No.   Shift δ (ppm)                                                                    Coupling .sup.1 Jcc (Hz)                      ______________________________________                                          A 1 125.6 J.sub.12 = 56.0                                                      3 155.0 J.sub.23 = 72.0                                                       4  10.1 J.sub.34 = 43.0                                                      B 1 127.8 J.sub.12 = 69.0                                                      3 452.1 J.sub.23 = 56.5                                                       4  14.4 J.sub.34 = 41.5                                                    ______________________________________                                    

                  TABLE 2.2                                                       ______________________________________                                        .sup.13 C-NMR shifts of methyl                                                  2-[[[(1-methyl-2-(4-(3-trifluoromethylphenylmethoxy)-                         phenyl)-2-E-[methoxyimino]ethylidene)amino]oxy]methyl]-                       α-(methoxymethylene)-phenylacetate (compound 1.225)                     #STR12##                                                                       -    Atom No. Shift δ (ppm)                                          ______________________________________                                        1            124.9                                                              2 155.1                                                                       3 155.0                                                                       4  11.1                                                                     ______________________________________                                    

What is claimed is:
 1. A process for the preparation of a compound ofthe formula ##STR13## and, where appropriate, their tautomers, in eachcase in the free form or salt form, in which eitherX is CH or N, Y isOR₁ and Z is O, or X is N, Y is NHR₈ and Z is O, S or S(═O); R₁ is C₁-C₄ alkyl; R₂ is H, C₁ -C₄ alkyl, halogeno-C₁ -C₄ alkyl, C₃ -C₆cycloalkyl or C₁ -C₄ alkoxymethyl; R₃ and R₄ independently of oneanother are H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, OH, CN, NO₂, a (C₁ -C₄alkyl)₃ --Si group, where the alkyl groups can be identical ordifferent, halogen, (C₁ -C₄ alkyl)S(═O)_(m), (halogeno-C₁ -C₄alkyl)S(═O)_(m), halogeno-C₁ -C₄ alkyl or halogeno-C₁ -C₄ alkoxy; R₅ isC₁ -C₆ alkyl, halogeno-C₁ -C₆ alkyl, C₁ -C₆ alkoxy, halogeno-C₁ -C₆alkoxy, C₁ -C₆ -alkylthio, halogen-C₁ -C₆ alkylthio, C₁ -C₆alkylsulfinyl, halogeno-C₁ -C₆ alkylsulfinyl, C₁ -C₆ alkyl-sulfonyl,halogeno-C₁ -C₆ alkylsulfonyl, C₁ -C₆ alkoxy-C₁ -C₆ alkyl, halogeno-C₁-C₆ alkoxy-C₁ -C₆ alkyl, C₁ -C₆ alkylthio-C₁ -C₆ alkyl, halogeno-C₁ -C₆alkylthio-C₁ -C₆ alkyl, C₁ -C₆ alkyl-sulfinyl-C₁ -C₆ alkyl, halogeno-C₁-C₆ -alkylsulfinyl-C₁ -C₆ alkyl, C₁ -C₆ -alkylsulfonyl-C₁ -C₆ alkyl,halogeno-C₁ -C₆ -alkylsulfonyl-C₁ -C₆ alkyl, C₁ -C₆ -alkylcarbonyl,halogeno-C₁ -C₆ -alkylcarbonyl, C₁ -C₆ -alkoxycarbonyl, halogeno-C₁ -C₆-alkoxycarbonyl, C₁ -C₆ -alkylaminocarbonyl, C₁ -C₄ -alkoxyiminomethyl;di(C₁ -C₆ alkyl)-aminocarbonyl, where the alkyl groups can be identicalor different; C₁ -C₆ -alkylaminothiocarbonyl; di(C₁ -C₆alkyl)-aminothiocarbonyl, where the alkyl groups can be identical ordifferent; C₁ -C₆ -alkylamino, di(C₁ -C₆ alkyl)-amino, where the alkylgroups can be identical or different; halogen, NO₂, CN, SF₅, thioamido,thiocyanatomethyl; an unsubstituted or mono- to tetrasubstituted C₁ -C₄alkylenedioxy group, where the substituents are selected from the groupconsisting of C₁ -C₄ alkyl and halogen; or QR₆, where, if n is greaterthan 1, the radicals R₅ can be identical or different; R₆ is C₂ -C₆alkenyl or C₂ -C₆ alkynyl, which are unsubstituted or substituted by 1to 3 halogen atoms; (C₁ -C₄ alkyl)₃ Si, where the alkyl groups can beidentical or different; CN; or an unsubstituted or mono- topentasubstituted C₃ -C₆ cycloalkyl, aryl or heterocyclyl group, wherethe substituents are selected from the group consisting of halogen, C₁-C₆ alkyl, halogeno-C₁ -C₆ alkyl, C₁ -C₆ alkoxy, halogeno-C₁ -C₆ alkoxy,phenoxy, naphthoxy and CN; A either is a direct bond, C₁ -C₁₀ alkylene,--C(═O)--,--C(═S)-- or halogeno-C₁ -C₁₀ alkylene and R₇ is a radicalR₁₀, or is C₁ -C₁₀ alkylene, --C(═O)--,--C(═S)-- or halogeno-C₁ -C₁₀alkylene and R₇ is OR₁₀, N(R₁₀)₂, where the radicals R₁₀ can beidentical or different, or --S(═O)_(q) R₁₀ ; R₈ is H or C₁ -C₄ alkyl; R₉is methyl, fluoromethyl or difluoromethyl; R₁₀ is H; an unsubstituted orsubstituted C₁ -C₆ alkyl, C₂ -C₆ alkenyl or C₂ -C₆ alkynyl group, wherethe substituents are selected from the group consisting of halogen; (C₁-C₄ alkyl)₃ Si, where the alkyl groups can be identical or different; C₃-C₆ cyclo-alkyl, which is unsubstituted or substituted by halogen; C₁-C₆ alkoxycarbonyl, which is unsubstituted or substituted by halogen;unsubstituted or substituted aryl, where the substituents are selectedfrom the group consisting of halogen, halogeno-C₁ -C₄ alkyl and CN; a(C₁ -C₄ alkyl)₃ Si group, where the alkyl groups can be identical ordifferent; C₃ -C₆ cycloalkyl, which is unsubstituted or substituted byhalogen; C₁ -C₆ alkoxycarbonyl which is unsubstituted or substituted byhalogen; or an unsubstituted or substituted aryl or heterocyclyl group,where the substituents are selected from the group consisting of halogenand halogeno-C₁ -C₄ alkyl; Q is a direct bond, C₁ -C₆ alkylene, C₁ -C₆alkenylene, C₂ -C₆ alkynylene, O, O(C₁ -C₆ alkylene), (C₁ -C₆alkylene)O, S(═O)_(p), S(═O)_(p) (C₁ -C₆ alkylene) or (C₁ -C₆alkylene)S(═O)_(p) ; m is 0, 1 or 2; n is 0, 1, 2, 3, 4 or 5; p is 0, 1or 2; and q is 0, 1 or 2, and the C═N double bond marked with E has theE configuration, in which process ##STR14## (1) a compound of formula(VIII) in which R₂, R₅ and n are as defined for formula (I), or apossible tautomer thereof, in each case in the free form or in saltform, is reacted with a C₁ -C₆ alkyl nitrite;(2) the resulting E-isomerof formula (VI) is reacted with a compound of the formula (VII) R₇--A--X₂, in which A and R₇ are as defined for formula (I) and X₂ is aleaving group; (3) reacting the resulting compound of formula (IV) inwhich R₂, R₅, A, R₇ and n are as defined for formula (I) and the C═Ndouble bond marked with E has the E configuration, or a possibletautomer thereof, in each case in the free form or in salt form, withhydroxylamine or a salt thereof; and (4) reacting the resulting compoundof formula (II) in which A, R₂, R₅, R₇ and n are as defined for formula(I) and the C═N double bond marked with E has the E configuration, or apossible tautomer thereof, in each case in the free form or in saltform, with a compound of the formula ##STR15## in which X, Y, Z, R₃, R₄and R₅ are as defined for formula (I) and X₁ is a leaving group, or atautomer thereof, in each case in the free from or in salt form, inorder to obtain the compound of formula (I).
 2. A process according toclaim 1, wherein a compound of the formula (III) in which X₁ is halogenis used.
 3. A process according to claim 1, wherein a compound of theformula (III) in which X₁ is chlorine is used.
 4. A process according toclaim 1, wherein the reaction of a compound of formula (II) with acompound of formula (III) is carried out in the presence of a base.
 5. Aprocess according to claim 4, wherein the reaction is carried out in thepresence of a base selected from the group consisting of alkali metaland alkaline earth metal hydroxides hydrides, amides, alkanolates,acetates, carbonates, dialkylamides and alkylsilylamides.
 6. A processaccording to claim 5, wherein the base is sodium hydride.
 7. A processaccording to claim 1, wherein a compound of the formula (VII) in whichX₂ is halogen is used.
 8. A process according to claim 1, wherein acompound of the formula (VII) in which X₂ is chlorine is used.
 9. Aprocess according to claim 1, wherein the reaction of the compound ofthe formula (VI) with the compound of the formula (VII) is carried outin the presence of a base.
 10. A process according to claim 9, whereinthe reaction is carried out in the presence of a base selected from thegroup consisting of alkali metal and alkaline earth metal hydroxides,hydrides, amides, alkanolates, acetates, carbonates, dialkylamides andalkylsilylamides.
 11. A process according to claim 1 for the preparationof a compound of the formula ##STR16## in which A, R₂, R₅, R₇ and n areas defined for formula (I) and the C═N double bond marked with E has theE configuration, which comprises reacting at 0-80° C. the compound ofthe formula ##STR17## in which R₂, R₅ and n are as defined for formula(I) and the C═N double bond marked with E has the E configuration, witha compound of the formula

    R.sub.7 --A--X.sub.2                                       (VII),

in which A and R₇ are as defined for formula (I) and X₂ is a leavinggroup.
 12. A process according to claim 11, wherein a compound of theformula (VII) in which X₂ is halogen is used.
 13. A process according toclaim 1 for the preparation of a compound of the formula ##STR18## inwhich A, R₂, R₅, R₇ and n are as defined for formula (I) and the C═Ndouble bond marked with E has the E configuration, which comprisesreacting at 0-80°C. the compound of the formula ##STR19## in which A,R₂, R₅, R₇ and n are as defined for formula (I) and the C═N double bondmarked with E has the E configuration, with hydroxylamine or a saltthereof.
 14. A process according to claim 13, wherein the reaction iscarried out with hydroxylamine hydrochloride.
 15. A process according toclaim 1 for the preparation of a compound of the formula ##STR20## inwhich R₂, R₅ and n are as defined for formula (I) and the C═N doublebond marked with E has the E configuration, which comprises reacting at0-80° C. the compound of the formula ##STR21## in which R₂, R₅ and n areas defined for formula (I), with a C₁ -C₆ alkylnitrite.
 16. A processaccording to claim 15, wherein the reaction is carried out in thepresence of a base.
 17. A process according to claim 1 for thepreparation of a compound of the formula (I), which comprises reactingthe compound of the formula (VI), with a compound of the formula (VII),and reacting it with hydroxylamine or a salt thereof, if appropriate inthe presence of a basic or acid catalyst, and further reacting thecompound thus obtainable, of the formula (II), with a compound of theformula (III).